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4-Amino-2,6-dichloropyrimidine is an organic compound. The molecule contains a pyrimidine ring, with one chlorine atom substituted at positions 2 and 6, and one amino atom substituted at position 4. The appearance is usually a white or light yellow solid. Soluble in some organic solvents such as ethanol, methanol, etc. Mainly used in organic synthesis, as an intermediate for drugs and pesticides, in the pharmaceutical field, it can be used to synthesize antiviral, anticancer and other drugs.
Additional information of chemical compound:
|
Chemical Formula |
C4H3Cl2N3 |
|
Exact Mass |
162.97 |
|
Molecular Weight |
163.99 |
|
m/z |
162.97(100.0%),164.97(63.9%),166.96 (10.2%), 163.97 (4.3%), 165.97 (2.8%), 163.97 (1.1%) |
|
Elemental Analysis |
C, 29.30; H, 1.84; Cl, 43.23; N, 25.62 |
|
Melting point |
258-267℃ |
|
Boiling point |
323.5±22.0℃(Predicted) |
|
Density |
1.606±0.06 g/cm3(Predicted) |
|
Storage conditions |
2-8℃ |
|
|
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4-Amino-2,6-dichloropyrimidine is an organic compound with unique chemical structure and properties, and has broad application prospects in multiple fields. The following is a detailed explanation of its purpose:
I. Applications in Medicinal Chemistry and Drug Discovery
4-Amino-2,6-dichloropyrimidine serves as a core building block for constructing pyrimidine-containing bioactive molecules in the pharmaceutical industry, with particularly intensive applications in the development of kinase inhibitors, ion channel modulators, and antitumor, antiviral, anti-inflammatory, and antibacterial agents.
Its structural advantages lie in:
The chlorine atoms at the 2- and 6-positions act as good leaving groups and can undergo stepwise nucleophilic substitution with various amines, alcohols, and thiols to enable precise structural modification.
The amino group at the 4-position can be further subjected to amidation, alkylation, cyclization, and other reactions to expand molecular diversity and meet the requirements for SAR (structure-activity relationship) optimization.
(1) Intermediate for Kinase Inhibitors
Kinases are key proteins in cellular signal transduction, and their abnormal activation is closely associated with cancer, inflammation, fibrosis, and other diseases. The pyrimidine ring is a privileged scaffold for many kinase inhibitors, and 4-amino-2,6-dichloropyrimidine is a critical starting material for constructing such scaffolds.
Using it as a raw material, hydrophobic groups such as aromatic amines and heterocyclic amines can be introduced via selective substitution, yielding compounds with highly selective inhibitory activity against JAK, EGFR, ERK, PI3K, Aurora kinases, and others.
In the development of JAK kinase inhibitors, this intermediate is frequently used to construct aminopyrimidine frameworks. Modification of substituents regulates subtype selectivity toward JAK1/JAK2/JAK3, enhancing anti-inflammatory efficacy while reducing off-target toxicity.In antitumor research, derivatives synthesized from 4-amino-2,6-dichloropyrimidine can selectively inhibit kinases related to tumor cell proliferation, block cell cycle progression, and induce apoptosis, making them promising drug candidates for the treatment of solid tumors and hematological malignancies.
(2) Intermediate for Cardiovascular Drugs
A representative application of this compound in cardiovascular therapeutics is as a key synthetic precursor for potassium channel openers such as Pinacidil.Potassium channel openers induce hyperpolarization of vascular smooth muscle cell membranes, dilate blood vessels, and reduce peripheral resistance; they are clinically used to treat hypertension, angina pectoris, and heart failure.
4-Amino-2,6-dichloropyrimidine forms pyrimidinamine structures with potassium channel-modulating activity by introducing lipophilic side chains and hydrogen-bond donor groups through nucleophilic substitution, making it an indispensable intermediate in the synthetic routes of such drugs.
In addition, some derivatives prepared from it show potential in antiarrhythmic therapy and alleviating myocardial ischemia-reperfusion injury, attracting attention in the development of anti-heart-failure medications.
(3) Antibacterial, Antiviral, and Antiparasitic Agents
Pyrimidine derivatives represent classic antimetabolite scaffolds for antibacterial and antiviral drugs.Through structural modification, 4-amino-2,6-dichloropyrimidine can interfere with nucleic acid synthesis and protein expression in pathogenic microorganisms, exerting inhibitory effects against bacteria, fungi, viruses, and parasites.
In antifungal applications, its derivatives target fungal cell wall synthesis and membrane stability, showing good activity against clinically common pathogenic fungi such as Candida and Aspergillus.
In antiviral research, compounds built from this intermediate inhibit key enzymes in viral replication, with potential activity against herpesviruses, retroviruses, and others.Meanwhile, certain derivatives are used in the development of antimalarial and anti-toxoplasma antiparasitic agents, acting by blocking the folate metabolic pathway of parasites.
(4) Anti-Inflammatory and Immunomodulatory Drugs
Given the close correlation between JAK kinases and inflammatory and autoimmune diseases, JAK inhibitor derivatives centered on 4-amino-2,6-dichloropyrimidine hold significant promise for treating autoimmune disorders including rheumatoid arthritis, psoriasis, and systemic lupus erythematosus.
These molecules reduce inflammatory tissue damage by inhibiting inflammatory cytokine signaling. Compared with traditional nonsteroidal anti-inflammatory drugs (NSAIDs), they exhibit higher targeting selectivity and fewer gastrointestinal side effects.
II. Applications in Pesticide Creation and Agrochemicals
4-Amino-2,6-dichloropyrimidine is an important intermediate for high-efficiency, low-residue agrochemicals, widely used in the research and development of fungicides, herbicides, and plant growth regulators.Pyrimidine-based pesticides have become a major direction in modern green pesticide development due to their favorable environmental compatibility, unique mechanisms of action, and safety toward non-target organisms.
(1) Fungicides
Pyrimidine fungicides synthesized from this intermediate primarily act by inhibiting the respiratory chain, cell wall synthesis, or nucleic acid metabolism of pathogens, providing excellent control over crop diseases caused by Oomycetes, Ascomycetes, Deuteromycetes, and others.
Their derivatives can be used to manage common diseases including rice sheath blight, wheat powdery mildew, downy mildew, and anthracnose in fruits and vegetables, featuring strong systemic conductivity, long duration, and resistance to rain wash.
By introducing different substituents on the pyrimidine ring, the fungicidal spectrum and systemic activity can be tuned to achieve efficient control of various fungal crop diseases. Some derivatives also induce plant disease resistance, enhancing crop immunity and supporting integrated disease management.
(2) Herbicides
Pyrimidinylurea and pyrimidinamine herbicides prepared from 4-amino-2,6-dichloropyrimidine exert weed control by inhibiting plant acetolactate synthase (ALS) or carotenoid biosynthesis, thereby interfering with weed growth and development.
These herbicides offer advantages such as high selectivity, low application rates, and safety for succeeding crops, making them suitable for weed control in major field crops including rice, corn, soybean, and wheat.
Compared with traditional herbicides, their derivatives are less prone to resistance development and can be used in resistant weed management, occupying an important position in modern integrated weed control systems.
(3) Plant Growth Regulators
Certain derivatives of 4-amino-2,6-dichloropyrimidine regulate endogenous plant hormone levels, promoting seed germination, root development, flowering, and fruit setting, or inhibiting excessive vegetative growth and improving stress resistance.
In agricultural production, they can be used to cultivate strong seedlings, increase yield, and improve fruit quality, with significant application potential especially in cash crops and protected cultivation.
III. Applications in Organic Synthesis and Materials Science
(1) Versatile Heterocyclic Building Block
4-Amino-2,6-dichloropyrimidine is an important platform compound for constructing complex heterocyclic molecules in organic synthesis.
The chlorine atoms at the 2,6-positions can undergo aromatic nucleophilic substitution, Suzuki coupling, Sonogashira coupling, and other reactions with amines, phenols, thiophenols, alkynes, boronate esters, etc., enabling efficient synthesis of polysubstituted pyrimidine derivatives.The amino group at the 4-position can participate in condensation, cycloaddition, diazotization, and other reactions to construct fused heterocyclic systems such as imidazopyrimidines, pyridopyrimidines, and triazolopyrimidines, which are widely used in drug library construction and total synthesis of natural products.
(2) Functional Materials and Organic Optoelectronic Materials
In materials science, this compound can serve as a structural unit for organic optoelectronic functional materials.Its pyrimidine ring exhibits favorable electron-transport properties. By introducing conjugated aromatic groups, it can be used to prepare functional layer materials for devices including organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and dye-sensitized solar cells (DSSCs).
Furthermore, its derivatives can be applied as metal ion chelating ligands, fluorescent probes, polymer crosslinking agents, and other functional materials, with expanding potential in analytical testing, polymer modification, and catalytic materials.
4-Amino-2,6-dichloropyrimidine, as an organic compound with unique chemical structure and properties, has shown extensive application potential in multiple fields. The following is a detailed analysis of its development prospects:
Market and Industry Analysis
Market demand growth
With the continuous development of industries such as pharmaceuticals, pesticides, dyes, etc., the demand for this substance will continue to grow. Especially in the fields of new drug research and development, efficient pesticide development, etc., its market demand will be even more vigorous. The growth of this market demand will drive the development and expansion of its industry.
Industrial technological progress
With the continuous advancement of science and technology and the deepening of people's understanding of its properties, its synthesis and application technologies will continue to be improved and perfected. For example, by optimizing the synthesis route, improving reaction efficiency, and reducing production costs, the yield and quality of the substance can be further improved. At the same time, by conducting in-depth research on its application mechanism and expanding its application fields, its potential can be further explored.
Industrial policy support
In order to promote the development of this industry, the government will introduce a series of industrial policy support measures. For example, providing policy support such as research funding, tax incentives, and market access, encouraging enterprises to increase their R&D investment and technological innovation efforts, and promoting the rapid development of their industries.
Policy and regulatory recommendations
Strengthen regulatory efforts: The government should strengthen the supervision of such harmful chemicals, formulate stricter emission standards and restriction measures. At the same time, supervision and inspection of production and use enterprises should be strengthened to ensure their compliance with relevant laws, regulations, and standards.
Promoting technological innovation: The government should increase its support for technological innovation and encourage research institutions and enterprises to conduct research on alternative substances and green chemistry for harmful chemicals. Through technological innovation, industrial upgrading and transformation can be promoted, and the safety and environmental friendliness of products can be improved.
Strengthen public education: The government should enhance public awareness and education on the safety and environmental protection of these harmful chemicals. By popularizing relevant knowledge, improving public awareness and understanding of hazardous chemicals, and enhancing their self-protection awareness and ability.
From the 1940s to the 1960s, organic heterocyclic chemistry entered a period of rapid development. Pyrimidine compounds became a research focus due to their vital roles in living organisms (e.g., as building blocks of nucleic acids), and researchers began to systematically explore synthetic methods for polysubstituted pyrimidines. During this stage, chemists had mastered basic pyrimidine ring synthesis techniques. While studying derivatization reactions of aminopyrimidines and halopyrimidines, they made the first attempts to prepare dichloro-substituted aminopyrimidine derivatives via chlorination.
Initially, 4-amino-2,6-dihydroxypyrimidine was used as the starting material and phosphorus oxychloride as the chlorinating agent to obtain crude 4-amino-2,6-dichloropyrimidine. However, limited by synthetic technology, the reaction conditions were crude with no efficient acid-binding agent, resulting in an extremely low product yield (below 40%) and high impurity content. Precise structural characterization could not be achieved; it was only identified as a pyrimidine derivative bearing an amino group at the 4-position and chlorine atoms at the 2- and 6-positions, and no in-depth research or application was carried out.
After the 1970s, modern analytical techniques (infrared spectroscopy, nuclear magnetic resonance, gas chromatography) became increasingly available, providing technical support for the structural identification of the compound.
Researchers optimized the chlorination conditions and introduced acid-binding agents such as triethylamine to reduce side reactions and improve product purity. The molecular structure was accurately confirmed as 4-amino-2,6-dichloropyrimidine, and its CAS Registry Number 10132-07-7 was officially registered, establishing it as a standardized organic intermediate.
During this period, patents began to report improvements to its synthetic process, including optimizing the molar ratio of phosphorus oxychloride to starting materials and controlling the reaction temperature at 20–80 °C, raising the yield to 70%–85%. Post-treatment steps were also simplified, solving the problem of crude product purification. In addition, researchers recognized the high reactivity of the amino group and the two chlorine atoms in the molecule, laying the foundation for subsequent application exploration and gradually attracting attention in the pharmaceutical and agrochemical fields.
In the early 21st century, surging demand for high-efficiency intermediates in pharmaceuticals and agrochemicals fully unlocked the application value of 4-amino-2,6-dichloropyrimidine, driving further optimization of its synthetic process.
Researchers developed a solvent-free, high-yield synthesis method using a combined chlorination system of phosphorus oxychloride and phosphorus pentachloride with efficient acid-binding agents. The product yield exceeded 90% and purity reached above 98%, enabling large-scale industrial production.
As a key intermediate, it has been widely used in the synthesis of sulfonamides, kinase inhibitors, pyrimidine fungicides, and herbicides, transforming from a laboratory reagent into a core raw material supporting the pharmaceutical and agrochemical industries. Today, with the advancement of green chemical technologies, its synthetic processes continue to evolve toward environmental friendliness and low energy consumption, while its application scenarios keep expanding, making it an important bridge connecting basic organic synthesis and high-end fine chemical engineering.
adverse reaction
4-Amino-2,6-dichloropyrimidine (CAS number: 10132-07-7) is a heterocyclic aromatic compound containing chlorine and amino groups, with a molecular formula of C ₄ H ∝ Cl ₂ N ∝ and a molecular weight of 163.99. Its physical properties are manifested as white to light brown crystalline powder, with a melting point of 258-267 ℃ and a density of 1.606 g/cm ³. It is slightly soluble in water at room temperature, but soluble in organic solvents such as dimethyl sulfoxide (DMSO) and N, N-dimethylformamide (DMF). This compound has high reactivity due to the amino group and two chlorine atoms on the pyrimidine ring, and can participate in substitution reactions, redox reactions, and polymerization reactions.
Acute toxic reaction
Oral toxicity
4-Amino-2,6-dichloropyrimidine is classified as a hazardous chemical and may cause acute poisoning when taken orally. According to the classification criteria of the Safety Data Sheet (SDS), its hazard declaration includes H302 (Harmful if swallowed). Animal experiments have shown that the median lethal dose (LD50) for non intestinal routes in mice is 2400 mg/kg, indicating that it has certain toxicity. After oral administration, the compound may be absorbed through the gastrointestinal tract, causing digestive symptoms such as nausea, vomiting, abdominal pain, and in severe cases, may cause liver function damage or central nervous system suppression.
Toxicity in contact with skin and mucous membranes
Direct contact with 4-Amino-2,6-dichloropyrimidine may cause skin and mucosal irritation. The hazard statements H315 (causing skin irritation) and H319 (causing severe eye irritation) clearly indicate their risks. After contact, the skin may experience redness, swelling, or burning sensation, while eye contact may lead to conjunctival congestion, tearing, and even corneal damage. Long term or repeated exposure may cause skin allergic reactions, such as contact dermatitis.
Inhalation toxicity
Inhaling the dust or vapor of this compound may cause irritation to the respiratory tract. Hazard statement H335 (may cause respiratory irritation) indicates that exposure to high concentrations may cause coughing, shortness of breath, or difficulty breathing. For individuals with asthma or chronic respiratory diseases, the risk may be higher.
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