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Method for synthesizing 2-amino-6-chloropurine

A technology of chloropurine and amino, which is applied in the field of synthesizing 2-amino-6-chloropurine, can solve the problems of low atom economy, many three waste products, strong corrosion, etc., and achieve short reaction time, high yield, and reaction The effect of fewer steps

Inactive Publication Date: 2020-08-28
SHANGHAI LINKCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A large amount of hexamethyldisilazane is used in this reaction, trimethylchlorosilane will be formed during the chlorination process, and the by-product is highly corrosive; hexamethyldisiloxane will be formed when the liquid caustic soda is hydrolyzed, and as the equipment grows Over time, the substance will form a layer of white deposits inside and outside the equipment, which is difficult to clean; and the use of hexamethyldisilazane makes the atom economy in the synthesis process not high, and there are many three waste products; patent EP0543095A2 reports, The intermediate 2-dimethylaminomethenimino-6-chloropurine is formed by reacting guanine and N,N-dimethylformamide under the action of a chlorinating agent, and then reacted with acetic acid to obtain 2-formamido -6-chloropurine, then alkalized to obtain crude product 2-amino-6-chloropurine, after recrystallization and purification to obtain fine 2-amino-6-chloropurine; this synthesis process will produce a large amount of three wastes, especially a large amount of trichloropurine Waste acid water produced by oxonphos and extensive use of N,N-dimethylformamide

Method used

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  • Method for synthesizing 2-amino-6-chloropurine

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Experimental program
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Effect test

Embodiment 1

[0022] A method for synthesizing 2-amino-6-chloropurine, comprising the steps of:

[0023] The first step: add 6-hydroxyl-2,4,5-triaminopyrimidine (120g) and trimethyl orthoformate (99.3g) into the reaction flask, slowly add 32% concentrated hydrochloric acid (145g) dropwise, and stir at room temperature 8 hours; add water (150g), neutralize pH7-8 with the liquid caustic soda of 2.5M, gained solid is filtered; At 40-45 degree, filter cake is beaten with water 1 hour; Filter and dry again, get white solid guanine ( 109g); second step: add guanine (100g) to 150.8g of 32% hydrochloric acid, control the temperature at 40~50°C, slowly add 30% hydrogen peroxide 75.1g dropwise, control the temperature at 40~50°C for 3 hours, and cool to 20 ℃ with 2.5M liquid caustic soda to neutralize the pH 6-7.5, filter with suction, and dry the product 2-amino-6-chloropurine (95.6g).

Embodiment 2

[0025] A method for synthesizing 2-amino-6-chloropurine, comprising the steps of:

[0026] The first step: 6-hydroxyl-2,4,5-triaminopyrimidine (120g) and trimethyl orthoformate (99.3g) were added in the reaction flask, slowly added dropwise 32% acetic acid (145g), stirred at room temperature for 8 Hour; Add water (150g), neutralize pH7-8 with the liquid caustic soda of 2.5M, gained solid is filtered; At 40-45 degree, filter cake is beaten with water 1 hour; Filter and dry again, get white solid guanine (109g ); second step: add guanine (100g) to 150.8g of 32% hydrochloric acid, control the temperature at 40-50°C, slowly add 30% hydrogen peroxide 75.1g dropwise, control the temperature at 40-50°C for 3 hours, and cool to 20°C Use 2.5M liquid caustic soda to neutralize pH 6-7.5, filter with suction, and dry the product 2-amino-6-chloropurine (94.1g).

Embodiment 3

[0028] A method for synthesizing 2-amino-6-chloropurine, comprising the steps of:

[0029] The first step: add 6-hydroxyl-2,4,5-triaminopyrimidine (120g) and trimethyl orthoformate (99.3g) into the reaction flask, slowly add 32% acetic anhydride (145g) dropwise, and stir at room temperature 8 hours; add water (150g), neutralize pH7-8 with the liquid caustic soda of 2.5M, gained solid is filtered; At 40-45 degree, filter cake is beaten with water 1 hour; Filter and dry again, get white solid guanine ( 109g); second step: add guanine (100g) to 150.8g of 32% hydrochloric acid, control the temperature at 40~50°C, slowly add 30% hydrogen peroxide 75.1g dropwise, control the temperature at 40~50°C for 3 hours, and cool to 20 ℃ with 2.5M liquid caustic soda to neutralize pH 6-7.5, filter with suction, and dry the product 2-amino-6-chloropurine (93.6g).

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Abstract

The invention discloses a method for synthesizing 2-amino-6-chloropurine, and belongs to the field of organic chemical synthesis. The synthesis method of the 2-amino-6-chloropurine comprises the following steps: enabling 6-hydroxyl-2,4,5-triaminopyrimidine to react with trimethyl orthoformate to generate guanine, and enabling the guanine to react with hydrogen chloride and hydrogen peroxide to generate 2-amino-6-chloropurine. The method has the advantages of short reaction time, high yield, no generation of a large amount of three wastes, simple operation, and facilitation of industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 2-amino-6-chloropurine, which belongs to the field of organic chemical synthesis. Background technique [0002] 2-Amino-6-chloropurine is an important intermediate in the synthesis of purine antiviral drugs famciclovir, penciclovir and valacyclovir, and can also be used in the synthesis of anticancer, hypotensive and anti-inflammatory drugs. Penciclovir (penciclovir), a nucleoside drug synthesized by 2-amino-6-chloropurine, can resist a variety of viruses, such as nuclear Pesse virus including herpes simplex virus (HSV-1, HSV-2), varicella zoster virus (VZV), Epstein-Barr virus (EBV), hepatitis B virus (HBV) and duck hepatitis B virus (DHBV), etc., and has the characteristics of long-lasting and stable efficacy. Purine nucleoside methylenecyclopropanes synthesized from 2-amino-6-chloropurine are resistant to human murine herpesviruses including human murine cytomegalovirus (HCMV, MCMV), EBV, HSV-1 and...

Claims

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Application Information

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IPC IPC(8): C07D473/40
CPCC07D473/40
Inventor 陆茜许东红崔赛德
Owner SHANGHAI LINKCHEM TECH CO LTD
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