Method for synthesizing 2-amido-6-chloropurine

A synthetic method, the technology of chloropurine, applied in the direction of organic chemistry, etc., can solve the problems of low product yield, side reactions, affecting the yield and purity of 2-amino-6-chloropurine, etc., and achieve a reasonable and high synthetic process. Yield effect

Inactive Publication Date: 2008-03-12
LIANYUNGANG CCA CHEM CO LTD
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  • Abstract
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Problems solved by technology

[0013] Compared with the aforementioned several synthetic methods, although the process is relatively reasonable and the product yield is relatively high, which can reach 60% to 70%, there are still some deficiencies, such as in the synthesis of guanine and N, N-di In this step reaction that methyl formamide generates 2-dimethylaminomethenimino-6-chloropurine under the action of chlorinating agent, owing to adopting the mode that all raw materials are added together, be unfavorable for N on the one hand, N-di Methylformamide reacts with phosphorus oxychloride first to generate the active intermediate of carbanion

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  • Method for synthesizing 2-amido-6-chloropurine
  • Method for synthesizing 2-amido-6-chloropurine
  • Method for synthesizing 2-amido-6-chloropurine

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Embodiment 1

[0045] The synthesis of embodiment one 2-amino-6-chloropurine (1)

[0046] The synthetic method of 2-amino-6-chloropurine (1) comprises the following steps successively:

[0047] a) Preparation of 2-dimethylaminomethenimino-6-chloropurine (3)

[0048] First add 40mL of N,N-dimethylformamide to the dry reaction bottle, and add 35mL of POCl dropwise at 0℃~10℃ 3 , formulated as POCl 3 N,N-dimethylformamide solution, set aside; then in another dry reaction bottle, add 200mL of 1,2-dichloroethane and 20g of guanine (2), at 20℃~30℃ , dropwise add the prepared N,N-dimethylformamide solution of phosphorus oxychloride. After dripping, keep stirring for 1 hour, then heat up and reflux for 5 to 8 hours to complete the reaction, and cool to obtain 2-dimethylaminomethenimino-6-chloropurine (3). The intermediate product (3) does not need to be prepared from the reaction solution Separated from, the reaction solution containing the intermediate product (3) is for subsequent use;

[0049...

Embodiment 2

[0056] The synthesis of embodiment two 2-amino-6-chloropurine (1)

[0057] The synthetic method of 2-amino-6-chloropurine (1) comprises the following steps:

[0058] a) Preparation of 2-dimethylaminomethenimino-6-chloropurine (3)

[0059] First add 40mL of N,N-dimethylformamide to the dry reaction bottle, and add 35mL of POCl dropwise at 0℃~10℃ 3 , formulated as POCl 3 N,N-dimethylformamide solution, set aside; then in another dry reaction bottle, add 200mL of 1,2-dichloroethane and 20g of guanine (2), at 20℃~30℃ , dropwise add the prepared N,N-dimethylformamide solution of phosphorus oxychloride. After dripping, keep stirring for 1 hour, then heat up and reflux for 5 to 8 hours to complete the reaction, and cool to obtain 2-dimethylaminomethenimino-6-chloropurine (3). The intermediate product (3) does not need to be prepared from the reaction solution Separated from, the reaction solution containing the intermediate product (3) is for subsequent use;

[0060] b) Preparat...

Embodiment 3

[0067] The synthesis of embodiment three 2-amino-6-chloropurine (1)

[0068] The synthetic method of 2-amino-6-chloropurine (1) comprises the following steps successively:

[0069] a) Preparation of 2-dimethylaminomethenimino-6-chloropurine (3)

[0070] First, add 40mL of N,N-dimethylformamide to the dry reaction bottle, and add 35mL of POCl dropwise at 0-10°C 3 , formulated as POCl 3 N,N-dimethylformamide solution, set aside; then in another dry reaction bottle, add 200mL of 1,2-dichloroethane and 20g of guanine (2), at 20℃~30℃ , dropwise add the prepared N,N-dimethylformamide solution of phosphorus oxychloride. After dripping, keep stirring for 1 hour, then heat up and reflux for 5 to 8 hours to complete the reaction, and cool to obtain 2-dimethylaminomethenimino-6-chloropurine (3). The intermediate product (3) does not need to be prepared from the reaction solution Separated from, the reaction solution containing the intermediate product (3) is for subsequent use;

[007...

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Abstract

The present invention relates to a synthesis method of the 2-amino-6-chlorine purine (1), orderly comprising the following steps: the N, N-dimethylformamide is first added in the phosphorus oxychloride at a low temperature to prepare the mixture solution; then the 1, 2-dichloromethane of the guanine (2) is dropped to react to get the 2-dimethylamino-ene imino-6-chlorine purine (3); the product (3) is dropped into the water; the organic phase is separated and recycled for reuse; the alkali metal hydroxide solution is used for adjusting the pH value of the water phase to be between 3 and 5; the 2- formamide-6-chlorine purine (4) wet material is produced after heating; the product (4) wet material is done with the hydrolysis reaction in the alkali metal hydroxide solution; then the hydrochloric acid is used for adjusting the pH value to get the crude material of the 2-amino-6-chlorine purine (1); finally the fine target product (1) can be got through purification.

Description

technical field [0001] The present invention relates to the synthesis method of 2-amino-6-chloropurine, 2-amino-6-chloropurine is an important intermediate for synthesizing the antiviral drug "Famciclovir" (Famciclovir), and can also be used for anticancer, anti-inflammatory and hypotensive Synthesis of other drugs. Background technique [0002] The English name of "Famciclovir" is Famciclovir, and its chemical name is 2-[2-(2-amino-9H-purin-9-yl)ethyl]-1,3-propanediol-diethyl ester. Poisonous anti-herpes virus drugs, mainly used for the treatment of herpes zoster and genital herpes. Its structural formula is as follows: [0003] [0004] And 2-amino-6-chloropurine is a very important pharmaceutical intermediate for the synthesis of "Famciclovir". There are many synthetic routes of 2-amino-6-chloropurine, and the disclosed synthetic routes are listed as follows: [0005] 1. Direct Chlorination of Guanine [0006] Patent WO93 / 15075 publicly reported that 2-amino-6-chl...

Claims

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Application Information

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IPC IPC(8): C07D473/40
Inventor 陈文华刘巧云丁敬敏仝礼任褚兵张婷
Owner LIANYUNGANG CCA CHEM CO LTD
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