6-Chloropurine CAS 87-42-3

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6-Chloropurine is an important purine derivative and an organic synthetic intermediate. Its structure is based on the purine nucleus, with one hydrogen atom replaced by a chlorine atom. The most notable characteristic of this compound lies in the high chemical reactivity of the chlorine atom at the C6 position in its molecule, which makes it easily substituted by various nucleophilic reagents (such as amines, alcohols, or thioalcohols), enabling the efficient and directed synthesis of a series of purine-based alkaloids, drug molecules, and bioactive compounds. Based on this key reactivity, it plays an indispensable and irreplaceable role in the fields of medicinal chemistry and organic synthesis. It is a key starting material and core building block for synthesizing numerous anti-cancer drugs (such as thiopurine), immunosuppressants, and antiviral agents. Additionally, as a halogenated analogue of adenine, it is also used as a probe or inhibitor in biochemical research to interfere with and explore the purine metabolic pathways and the biosynthesis process of nucleic acids, demonstrating its dual value of connecting basic research and clinical application.

6-Chloropurine is a highly representative synthetic block and biologically active molecule in purine heterocyclic compounds, with core applications focused on the synthesis of pharmaceutical intermediates, research and development of anti-tumor/antiviral drugs, biochemical and molecular biology research, and organic synthetic chemistry. The high reactivity of its 6-position chlorine atom makes it a key precursor for constructing various purine derivatives, which can be converted into core molecules such as adenine, 6-mercaptopurine, nucleoside analogues, etc. through nucleophilic substitution, coupling reactions, etc; At the same time, its own and metabolic products have biological activities that inhibit purine metabolism and interfere with nucleic acid synthesis, showing important potential in the treatment of diseases such as tumors and viral infections.

Synthesis of adenine and vitamin B4 (adenine phosphate)

 

Adenosine (6-aminopurine) is the core component of nucleic acids and coenzymes (such as ATP, NAD ⁺), as well as the parent structure of vitamin B4 (adenine phosphate). 6-chloropurine is the most important industrial intermediate for the synthesis of adenine.
Synthesis pathway: It undergoes a 6-position nucleophilic substitution reaction with ammoniating reagents such as ammonia and methylamine under heating and pressure conditions, where the chlorine atom is replaced by an amino group, directly generating adenine; Adenosine is phosphorylated to obtain vitamin B4 (adenine phosphate), which has high yield and easy purity control, and is the mainstream route for global vitamin B4 production.

Application value: Vitamin B4 is used to prevent and treat leukopenia and acute granulocytopenia, especially for leukopenia caused by tumor chemotherapy and radiotherapy; Adenosine is the basic raw material for synthesizing various nucleoside drugs and coenzyme preparations. The large-scale production of this substance directly supports the stability of the supply chain of vitamin B4 and related pharmaceutical products.

Synthesis of 6-mercaptopurine (6-mep) and thiopurine antitumor drugs

 

6-mercaptopurine (6-MP) is a classic purine based anti metabolic and anti-tumor drug used for the treatment of acute lymphocytic leukemia, chronic myeloid leukemia, and other conditions. This substance is a key precursor for the synthesis of 6-MP.
Synthesis mechanism: It reacts with thio reagents such as sodium hydrosulfide and thiourea, and the chlorine atom at position 6 is replaced by a thiol group (SH) to generate 6-mercaptopurine; The reaction conditions are mild and highly selective, making it the core step in the industrial production of 6-MP.

Extended applications: 6-MP can be further modified to synthesize derivatives such as azathioprine and mercaptopurine methylates. Among them, azathioprine is a commonly used immunosuppressant in clinical practice, used for the treatment of autoimmune diseases such as rheumatoid arthritis and systemic lupus erythematosus. It also indirectly supports the full industry chain research and production of thiopurine drugs through 6-MP.

Synthetic nucleoside antiviral/anti-tumor drugs

 

Nucleoside analogues are an important category of antiviral and anti-tumor drugs, with the structural core being the "base ribose/deoxyribose" unit. As a precursor of purine bases, it can be coupled with ribose, deoxyribose, and their derivatives to synthesize various nucleoside drug intermediates.
Adefovir dipivoxil related intermediate: Adefovir dipivoxil is an anti hepatitis B virus drug developed by Gilead Science. It blocks virus replication by inhibiting hepatitis B virus DNA polymerase. Its molecular structure contains adenine base, which is the key raw material for the synthesis of the drug's adenine unit. The drug core skeleton is constructed through ammoniation, alkylation and other steps.

Other nucleoside analogues: It undergoes 9-position N-alkylation reaction with glycosides/glycosides such as ribose and cyclopentyl groups to synthesize 9-alkyl-6-chloropurine, which is then substituted and modified to obtain intermediates of anti-tumor nucleoside analogues such as capecitabine and fludarabine; Meanwhile, carbon cyclic nucleoside analogues such as 9-norbornene-6-chloropurine derived from 6-chloropurine exhibit significant inhibitory activity against RNA viruses such as Coxsackievirus and rhinovirus, making them important lead compounds for antiviral drug development.

Self anti-tumor activity and mechanism of action

 

The substance itself has moderate anti-tumor activity and has shown inhibitory effects on cell proliferation and induction of apoptosis in various tumor models. Its mechanism of action is closely related to metabolic transformation and purine metabolism interference.
Metabolic activation mechanism: It can be metabolized through two core pathways in the body: ① Glutathione S-transferase (GST) catalyzes and binds with glutathione (GSH) to produce S-purine glutathione, which is further metabolized into 6-mercaptopurine (6-mep).

6-mep is activated by xanthine guanine phosphoribosyltransferase (HGPRT) to produce thioinosine acid (TIMP), which is ultimately converted into thioguanine nucleotides (TGNs).TGNs are incorporated into DNA/RNA, leading to chain breakage, inhibition of nucleic acid synthesis, and induction of tumor cell apoptosis; ② Oxidized by xanthine oxidase (XO) to 6-chlorouric acid, 6-chlorouric acid can competitively inhibit uricase and interfere with purine metabolism pathways.

Synergistic anti-tumor effect: When used in combination with Azaserine, a purine synthesis inhibitor, it exhibits significant synergistic anti-tumor effects in mouse leukemia and lymphoma models. Azaserine inhibits de novo purine synthesis, and 6-chloropurine metabolites interfere with nucleic acid replication, enhancing the killing efficiency of tumor cells.

Preclinical research data: In vitro experiments have shown that this substance has an IC50 value of approximately 10-50 μ M for human leukemia CCRF-CEM cells and HL-60 cells, and an IC50 value of approximately 32 μ M for liver cancer HepG2 cells. It has low toxicity to normal cells and has certain tumor selectivity.

Antiviral activity of derivatives

 

Its 9-alkylated and arylated derivatives have broad-spectrum antiviral activity, especially significant against RNA viruses.
Antienterovirus activity: 9-de-6-chloropurine (NCP) is a typical representative, which has a strong inhibitory effect on small RNA viruses such as Coxsackievirus B group and rhinovirus. Its mechanism may be to block viral RNA replication and interfere with viral capsid assembly;

In vitro experiments have shown that NCP has an EC50 of approximately 0.5 μ M for Coxsackievirus B3 and low cytotoxicity (CC50>100 μ M), indicating its potential as an antiviral drug.
Antiherpesvirus activity: This substance is coupled with an acyclic guanosine analogue to synthesize purine acyclic nucleoside derivatives, which have inhibitory activity against herpes simplex virus (HSV) and varicella zoster virus (VZV), and can be used as a complementary candidate for nucleoside antiviral drugs.

Reference information source：

1. Sigma Aldrich. 6-Chloropurine Product Manual [EB/OL]. (2026-01-14) [2026-03-19] https://www.sigmaaldrich.com/US/en/product/aldrich/511617
2. MolAid. Physical and Chemical Properties and Applications of 6-Chloropurine (CAS: 87-42-3) [EB/OL]. (2025-09-25) [2026-03-19] https://www.molaid.com/MS_145180
3. BenchChem Technical Support Team. A Comparative Cytotoxicity Analysis: 6‑Chloropurine vs. its Thio‑analog 6‑Mercaptopurine[R]. BenchChem, 2025. https://pdf.benchchem.com/169/A_Comparative_Cytotoxicity_Analysis_6_Chloropurine_vs_its_Thio_analog_6_Mercaptopurine.pdf
4. Elion, G. B., et al. On the Metabolic Effects of 6‑Chloropurine[J]. Cancer Research, 1961, 21(8): 1047‑1056. https://aacrjournals.org/cancerres/article ‑pdf/21/8/1047/2376753/crs0210081047.pdf
5. Hwang, Y. I., et al. Detection and mechanisms of formation of S‑(6‑purinyl)glutathione and 6‑mercaptopurine in rats given 6‑chloropurine[J]. Journal of Pharmacology and Experimental Therapeutics, 1993, 264(1): 41‑46.
6. Novakova, L., et al. 9‑Norbornyl‑6‑chloropurine Is a Novel Antileukemic Compound Interacting with Cellular GSH[J]. Anticancer Research, 2013, 33(8): 3163‑3170. https://ar.iiarjournals.org/content/33/8/3163

There are many ways to synthesize 6-Chloropurine, the following are the most commonly used methods:

Method 1: Hoffmann reaction:

This is the traditional method for preparing it. In this method, 2-amino-6-chloropurine is heated to 85 °C in NaOH solution, followed by mesophase formation, and then hydrolyzed in a polar solvent for 30 min. The product of hydrolysis is it.

Method 2: Fluoride substitution reaction:

This is a recently discovered synthetic method that can be used to produce. In this method, 2-aminopurine is reacted to produce N4-ethyl-2-aminopurine. Reaction of this compound with aluminum chloride triflate and ferric chloride as catalysts gives it.

Method 3: Catalytic chlorination of alcohols:

This method is a relatively simple method and can also be used to prepare product. In this method, 2-aminopurine is reacted with benzyl alcohol in tetrahydrofuran. This yields N4-benzyl alcohol or N4-tert-butanol-2-aminopurine. This compound was reacted further, adding excess ferrous chloride and silver chloride as catalysts. This reaction produces a chlorinated product as a product.

Method Four: Pyridine Catalyzed Chlorination:

Here is another way to synthesize 6-Chloropurine. In this method, 2-aminopurine and potassium ferrocyanate are reacted in a solution of pyridine. This compound will generate it by adding excess sodium hydroxide and hydrogen chloride gas.

In summary, it is an important organic compound, and there are many synthetic methods to choose from. Although the traditional Hoffmann reaction is the most commonly used method for preparing product, other simpler and more efficient methods have been discovered in recent years. Different preparation methods will produce different yields and wastes in different situations, so it is particularly important to choose the appropriate synthesis method according to the specific application scenario.

stability:

It is relatively stable at room temperature, but it is prone to decomposition or oxidation reaction under conditions such as light or heat. Under the action of strong oxidizing agents, it can be oxidized to 6-chlorouracil. In addition, the decomposition products of it may release toxic gas, so it is necessary to pay attention to safe handling.

Restorability:

It can react with reducing agents and can be reduced to 6-chloro-9H-purine under appropriate conditions. The reduction reaction needs to be carried out under an inert atmosphere and at low temperature.

Electrophilicity:

it can be functionally modified by substitution reaction and aromatic NMR substitution reaction. For example, it can react with amines to introduce new substituents at the 6-position. In addition, sodium trifluoromethanesulfonate can introduce aryl groups such as phenyl at the 6-position.

Acidity and alkalinity:

6-Chloropurine has relatively neutral acid-base properties and can accept or release protons under the action of strong acids or bases. In water, it has a pKa of 7.02. In the presence of a weak base, it can form ketal compounds, and the reaction needs to be carried out under alkaline conditions.

Stability: Comprehensive consideration from storage conditions to reaction activity

Physical stability

Melting point and boiling point: The melting point is above 300°C (decomposition), and the boiling point is 449.6 ± 25.0°C, indicating that it is in a solid state at room temperature and has high thermal stability;

Solubility: Soluble in water, ether and dimethylformamide (DMF), with a solubility of 30 mg/mL in DMSO at 25°C, and attention should be paid to the impact of solvent selection on reaction efficiency.

Chemical stability

Phototoxicity: This substance is sensitive to light, and long-term exposure to light may lead to degradation, and it should be stored in a dark place (such as using a brown reagent bottle);

Heat decomposition risk: May decompose and produce toxic gases (such as carbon monoxide, carbon dioxide, nitrogen oxides) at high temperatures, and should be kept away from fire sources and high-temperature environments;

Oxidation reaction: May be oxidized by strong oxidants (such as potassium permanganate) in the presence of strong oxidants, and should avoid mixed storage.

Optimization of storage conditions

Temperature control: Short-term storage can be placed in a 4°C refrigerator, and long-term storage should be frozen at -20°C or below to delay degradation;

Packaging requirements: Use sealed glass or polyethylene containers, avoid contact with metal ions (such as iron, copper), and prevent catalytic degradation;

Stability period: Under recommended storage conditions, the validity period is usually over 4 years, but regular purity and impurity content testing is required.

Reaction activity and compatibility

Acid-base stability: May undergo ring-opening or hydrolysis reactions in acidic or alkaline conditions, and pH control is required;

Metal catalysis: Contact with certain metals (such as palladium, nickel) may cause catalytic degradation, and an inert catalyst should be selected; Biological activity: As a synthetic intermediate, 6-chloropurine can be used to prepare anti-tumor drugs (such as 6-mercaptopurine) and antibacterial agents. Its reactivity directly affects the purity of the target product.

Safety and stability practices in industry applications

 

Pharmaceutical synthesis field

As the precursor of adenine and 6-mercaptopurine, its stability directly affects the purity of the drug. During the production process, strict monitoring of temperature, light exposure, and humidity is required to avoid side reactions;

Case: A pharmaceutical company experienced product degradation due to temperature fluctuations during storage, and ultimately solved the problem by optimizing the freezing storage conditions.

Biochemical research field

When used in the synthesis of 9-alkylpurine and 6-mercaptopurine, the purity of reagents (≥98%) must be ensured to avoid interference from impurities in the experimental results;

Safety advice: Laboratories should be equipped with biosafety cabinets, and operators should receive professional training to reduce the risk of long-term exposure.

Industrial production optimization

By using inert gas protection and automated control systems, the risk of human operation can be significantly reduced, while improving product stability;

Trend: The promotion of green chemical processes (such as solvent-free synthesis) is expected to further reduce safety and environmental pressure.

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