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2-Amino-4-chloropyrimidine is an organic compound with a Molecular formula of C4H4ClN3 and CAS 3993-78-0. It is a white solid crystal with no obvious odor. The melting point is usually within the range of 165-170 ° C. Information about its boiling point may be limited, but since the compound is a solid, its boiling point may be higher. It is soluble in many organic solvents at room temperature, such as ethanol, di N-Methylformamide (DMF) and dichloromethane. It has a low solubility in water. Relatively stable under conventional experimental conditions, but contact with oxidants or strong acids should be avoided to prevent unnecessary reactions. It may be sensitive to ultraviolet light or other radiation, so care should be taken to avoid light during storage and processing. It is an important intermediate in chemical synthesis and can be used to synthesize various organic compounds. It can be used as an aminating agent to react with other compounds in organic synthesis to form new Chemical bond. It can also be used as a standard in chemical analysis, for instrument calibration, drug detection, and other chemical analysis techniques. It can also be used for pesticide synthesis and for controlling various pests in agriculture.
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Chemical Formula |
C4H4ClN3 |
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Exact Mass |
129 |
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Molecular Weight |
130 |
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m/z |
129 (100.0%), 131 (32.0%), 130 (4.3%), 132 (1.4%), 130 (1.1%) |
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Elemental Analysis |
C, 37.09; H, 3.11; Cl, 27.36; N, 32.44 |
Molecular analysis of the structure of 2-Amino-4 chloropyrimidine:
1. Molecular formula: C4H4ClN3
The Molecular formula of 2-Amino-4-chloropyrimidine indicates the type and quantity of its constituent elements, including four carbon atoms (C), four hydrogen atoms (H), one chlorine atom (Cl) and three nitrogen atoms (N).
2. Molecular weight: 127.55 g/mol
By calculating the sum of the relative atomic masses of each element, the molecular weight of 2-Amino-4 chloropyrimidine can be obtained. In this case, the relative atomic mass of carbon is 12.01 g/mol, hydrogen is 1.008 g/mol, chlorine is 35.45 g/mol, and nitrogen is 14.01 g/mol.
3. Structural features:
2-Amino-4 chloropyrimidine is a compound containing a pyrimidine ring, with two amino (NH2) groups and one chlorine atom (Cl) substituted on the pyrimidine ring. The chlorine atom replaces the carbon atom 4 on the pyrimidine ring, while the amino group is located at positions 2 and 6.
This compound has a planar configuration, where the pyrimidine ring is flat, and the amino and chlorine atoms are located above or below the plane. The structure of 2-Amino-4 chloropyrimidine makes it widely used in organic synthesis and can be used as an intermediate for synthesizing other compounds.
2-amino-4 chloropyrimidine, as an important organic synthesis intermediate, has a wide range of applications in drug synthesis. Here are several typical application examples:
Antibacterial agents
2-Amino-4 chloropyrimidine and its derivatives can be used as active ingredients in antibacterial agents for the synthesis of various antibacterial drugs. These antibiotics have significant inhibitory effects on a variety of bacteria and can be used to treat various bacterial infectious diseases. For example, by introducing different substituents, drug molecules with broad-spectrum antibacterial activity can be synthesized for the treatment of various bacterial infections such as respiratory, digestive, and urinary tract infections.
Insecticide
2-Amino-4 chloropyrimidine can also be used for synthesizing insecticides. These insecticides have efficient killing effects on various pests and can be used for pest control in agriculture and forestry. By introducing specific substituents, the insecticidal spectrum and activity of insecticides can be adjusted to meet the needs of different environments and crops.
Enzyme inhibitor
2-amino-4-chloropyrimidine and its derivatives also play an important role in the synthesis of enzyme inhibitors. Enzyme inhibitors are a class of compounds that can inhibit enzyme activity and can be used to treat various enzyme related diseases. For example, by synthesizing enzyme inhibitors containing product structures, the activity of specific enzymes can be inhibited, thereby regulating relevant metabolic pathways in the body and achieving the goal of treating diseases.
Antitumor drugs
In recent years, research has found that 2-amino 4-chloropyrimidine and its derivatives have potential application value in the synthesis of anti-tumor drugs. These compounds can inhibit the proliferation and spread of tumor cells and have significant anti-tumor activity. Through further research and optimization, it is expected to develop new and efficient anti-tumor drugs, providing new options for cancer treatment.
The wide application of 2-amino-4 chloropyrimidine and its derivatives in drug synthesis is closely related to their unique chemical structure and biological activity. The following are the main mechanisms of action of 2-amino-4 chloropyrimidine in drug synthesis:
Inhibit enzyme activity
2-Amino-4 chloropyrimidine and its derivatives can inhibit enzyme activity by binding to enzymes. Enzymes are important proteins that catalyze chemical reactions in living organisms, and their activity is influenced by various factors. 2-Amino-4 chloropyrimidine can bind to the active center of the enzyme, alter its conformation, and thus inhibit its catalytic activity. This inhibitory effect can be used to treat various enzyme related diseases, such as inflammation, tumors, etc.
Inhibit cell proliferation
2-Amino-4 chloropyrimidine and its derivatives have inhibitory effects on cell proliferation. Cell proliferation is the foundation of biological growth and development, but it is also an important process in the occurrence and development of tumors. 2-Amino-4 chloropyrimidine can interfere with the signaling pathway of cell proliferation and inhibit the proliferation and spread of tumor cells. This inhibitory effect can be used to treat a variety of tumor diseases, such as lung cancer, breast cancer, etc.
Regulating immune response
2-amino 4-chloropyrimidine and its derivatives can also exert therapeutic effects by regulating immune responses. Immune response is an important defense mechanism of organisms against pathogens and foreign substances. However, in some cases, the immune response may be overactivated or dysregulated, leading to autoimmune diseases or inflammatory reactions. 2-amino-4 chloropyrimidine can regulate the activity and function of immune cells, inhibit overactivated immune responses, and alleviate symptoms of inflammation and autoimmune diseases.
Regulating immune response
2-amino 4-chloropyrimidine and its derivatives can also exert therapeutic effects by regulating immune responses. Immune response is an important defense mechanism of organisms against pathogens and foreign substances. However, in some cases, the immune response may be overactivated or dysregulated, leading to autoimmune diseases or inflammatory reactions. 2-amino-4 chloropyrimidine can regulate the activity and function of immune cells, inhibit overactivated immune responses, and alleviate symptoms of inflammation and autoimmune diseases.
Inhibit DNA replication
2-amino-4 chloropyrimidine and its derivatives can also inhibit the process of DNA replication. DNA replication is the foundation of genetic information transmission in organisms, but it is also an important process for virus replication and tumor cell proliferation. 2-Amino 4-chloropyrimidine can bind to DNA polymerase, inhibit its activity, and thus block the DNA replication process. This inhibitory effect can be used to treat various viral and tumor diseases.
There are various methods for synthesizing 2-amino-4-chloropyrimidine, including the following:
Method 1: Starting from Isocytosine
Reacting isocytosine with phosphorus oxychloride, the target compound 2-amino-4 chloropyrimidine is prepared through chlorination reaction. The specific experimental procedure is as follows:
Add phosphorus oxychloride and isocytosine to the reaction vessel, stir and raise the temperature to 80 ℃, and keep it at that temperature for 1 hour; After the insulation is completed, continue to heat up to 120 ℃ and maintain reflux for 3 hours. Absorb the tail gas from the reaction process with water to obtain hydrochloric acid byproduct. After the reaction is complete, the reaction solution is distilled to recover the oxygen and phosphorus in the reaction solution. Drop the reaction solution for removing oxygen and phosphorus into ice water, and control the drop temperature below 40 ℃. After complete dropwise addition, dichloromethane was added for multi-stage extraction to obtain a liquid phase and a lower liquid phase of dichloromethane. Add activated carbon to the lower dichloromethane liquid phase for decolorization and impurity removal, filter and heat to 40 to 60 ℃ to remove dichloromethane, then add 80 grams of ethanol and stir for 1 hour, cool to below 0 ℃ and crystallize for 2 hours. After filtration, obtain white solid 2-amino-4 chloropyrimidine with a yield of 76.4%.
Method 2: Starting from 2,4-dichloropyrimidine
Prepare 2-amino-4 chloropyrimidine by ammonolysis reaction between 2,4-dichloropyrimidine and ammonia water. The specific experimental procedure is as follows:
Add 2,4-dichloropyrimidine and ammonia water to a three necked flask, stir and reflux the reaction for 3 to 5 hours, and track the completion of the reaction by TLC. Cool the reaction solution to room temperature and filter it. The crude product was washed successively with ethanol (200mL) and water (500mL), dried, and then recrystallized using a mixed solvent of V (chloroform): V (petroleum ether)=1:1. After drying, a white solid 2-amino-4 chloropyrimidine was obtained with a yield of 84.4%.
Other synthesis methods
In addition to the above methods, 2 amino-4-chloropyrimidine can also be synthesized through other pathways. For example, 2-Amino 4-chloropyrimidine is synthesized from 2-nitro-3H-4-hydroxypyrimidine through steps such as chlorination and reduction. Alternatively, 2-amino-4-hydroxypyrimidine can be used as a raw material and heated in the presence of phosphorus oxychloride and nitrogen dimethylaniline to produce 2-amino 4-chloropyrimidine.
2-Amino-4-chloropyrimidine is a unique and important organic compound in the field of chemistry, with specific functional groups in its structure endowing it with a series of special chemical properties.
Acidic and alkaline characteristics:
The amino (NH2) portion of 2-amino 4-chloropyrimidine molecule exhibits alkalinity due to the lone pair electrons on its nitrogen atom. This alkalinity allows it to undergo neutralization reactions with acids (such as hydrochloric acid, sulfuric acid, etc.) in aqueous solutions, generating corresponding salts. This process not only changes the physical properties of the original compound (such as solubility, melting point, etc.), but may also affect its biological or reactive activity. It is worth noting that the reaction with strong acids is usually more complete, and the generated salts are stable and easy to separate and purify.
Redox properties:
In addition to the above properties, the amino and chlorine atoms in 2-amino 4-chloropyrimidine also have certain redox properties. Under the action of appropriate oxidants or reducing agents, they can undergo electron gain and loss, leading to changes in molecular structure. This redox property not only enriches the chemical behavior of the compound, but also provides the possibility to adjust its physical properties and biological activity through chemical modification. For example, amino groups can be converted to nitro groups through oxidation reactions, thereby changing the polarity and solubility of compounds; And through reduction reaction, halogens on chlorine atoms can be removed, generating corresponding alcohols or hydrocarbons.
What are the side effects of this compound?
If the compound is used as a pharmaceutical ingredient or active substance, its possible side effects may include:
Neurological effects:
Compounds with similar structures may sometimes have certain effects on the nervous system, such as headaches, dizziness, insomnia, hand tremors, etc.
Skin and mucosal irritation:
Certain compounds may cause irritation to the skin and mucous membranes, leading to redness, swelling, pain, or allergic reactions.
Digestive system effects:
Symptoms of digestive discomfort such as nausea, vomiting, and diarrhea may also occur.
Other potential effects:
Long term or excessive use may also have adverse effects on liver and kidney function, blood system, etc.
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