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Synthesis method of 4-amino-2,6-dimethoxyl pyrimidine

A technique for the synthesis of dimethoxypyrimidine and its synthesis method, which is applied in the field of synthesis of 4-amino-2.6-dimethoxypyrimidine, and can solve the problems of low yield in the chlorination step, increased process risk, and a large amount of phosphorous-containing wastewater. , to achieve the effects of less environmental pollution, avoiding emissions, and saving costs

Active Publication Date: 2020-04-10
YANGZHOU TIANHE PHARM CO LTD
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  • Claims
  • Application Information

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Problems solved by technology

This method synthetic route is simple, and by-product is few, but the yield of chlorination step is relatively low (being 44% to 81%), and the highly toxic phosphorus oxychloride is used in the preparation process, aftertreatment can produce a large amount of phosphorus-containing waste water, Not only increased the risk of the process, but also caused environmental pollution

Method used

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  • Synthesis method of 4-amino-2,6-dimethoxyl pyrimidine
  • Synthesis method of 4-amino-2,6-dimethoxyl pyrimidine
  • Synthesis method of 4-amino-2,6-dimethoxyl pyrimidine

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Experimental program
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Effect test

Embodiment 1

[0031] A kind of synthetic method of 4-amino-2.6-dimethoxypyrimidine, comprises the steps:

[0032] (1) Add 300ml of water and 26.5g of 28% ammonia water into a 500mL four-necked reaction flask, add 40g of 4,6-dichloropyrimidine-5-carboxylic acid under stirring, then keep warm at 30°C and react for 6 hours to obtain 4-amino- 6-chloropyrimidine-5-carboxylic acid;

[0033] (2) After the reaction finishes, adjust the pH of 4-amino-6-chloropyrimidine-5-formic acid to 3 with hydrochloric acid, pass into about 15g of chlorine gas, control the temperature during the process of flowing chlorine gas between 10~40°C, and end the flow of chlorine gas, Use liquid caustic soda to adjust the pH to 4-5, and filter below 20°C to obtain the wet product of 4-amino-2,6-dichloropyrimidine-5-carboxylic acid;

[0034] (3) Add 1000ml of water into a 2L pressure reactor, put in the 4-amino-2,6-dichloropyrimidine-5-carboxylic acid obtained in step (2), raise the temperature to 150°C, react for 2 hour...

Embodiment 2

[0037] A kind of synthetic method of 4-amino-2.6-dimethoxypyrimidine, comprises the steps:

[0038] (1) Add 300ml of water and 32.7g of 28% ammonia water into a 500mL four-necked reaction flask, add 40g of 4,6-dichloropyrimidine-5-carboxylic acid under stirring, then keep warm at 50°C and react for 12 hours to obtain 4-amino- 6-chloropyrimidine-5-carboxylic acid;

[0039] (2) After the reaction finishes, adjust the pH of 4-amino-6-chloropyrimidine-5-formic acid to 3 with hydrochloric acid, pass into about 15g of chlorine gas, control the temperature during the process of flowing chlorine gas between 10~40°C, and end the flow of chlorine gas, Use liquid caustic soda to adjust the pH to 4-5, and filter below 20°C to obtain the wet product of 4-amino-2,6-dichloropyrimidine-5-carboxylic acid;

[0040] (3) Add 1000ml of water into a 2L pressure reactor, put in the wet product of 4-amino-2,6-dichloropyrimidine-5-carboxylic acid obtained in step (2), raise the temperature to 110°C, ...

Embodiment 3

[0043] A kind of synthetic method of 4-amino-2.6-dimethoxypyrimidine, comprises the steps:

[0044] (1) Add 300ml of water and 32.7g of 28% ammonia water into a 500mL four-necked reaction flask, add 40g of 4,6-dichloropyrimidine-5-carboxylic acid under stirring, then keep warm at 50°C and react for 12 hours to obtain 4-amino- 6-chloropyrimidine-5-carboxylic acid;

[0045](2) After the reaction finishes, adjust the pH of 4-amino-6-chloropyrimidine-5-formic acid to 3 with hydrochloric acid, pass into about 15g of chlorine gas, control the temperature during the process of flowing chlorine gas between 10~40°C, and end the flow of chlorine gas, Use liquid caustic soda to adjust the pH to 4-5, and filter below 20°C to obtain the wet product of 4-amino-2,6-dichloropyrimidine-5-carboxylic acid;

[0046] (3) Add 1000ml of water into a 2L pressure reactor, put in the wet product of 4-amino-2,6-dichloropyrimidine-5-carboxylic acid obtained in step (2), raise the temperature to 110°C, r...

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Abstract

The invention discloses a synthesis method of 4-amino-2,6-dimethoxyl pyrimidine, and belongs to the technical field of medical technologies. The synthesis method comprises following steps: (1) aminolysis reaction: adding 4,6-dichloropyrimdine-5-formic acid into ammonia liquor to carry out aminolysis reactions to obtain 4-amino-6-chloropyrimdine-5-formic acid; (2) chlorination reaction: dissolving4-amino-6-chloropyrimdine-5-formic acid prepared in the step (1) in a water solution of a diluted acid, then adding a chlorination reagent, and carrying out chlorination reactions to obtain 4-amino-2,6-chloropyrimdine-5-formic acid; (3) decarboxylation reaction: in a solvent, carrying out high temperature decarboxylation of 4-amino-2,6-chloropyrimdine-5-formic acid prepared in the step (2) to obtain 4-amino-2,6-chloropyrimdine; and (4) methoxylation reaction: adding 4-amino-2,6-chloropyrimdine prepared in the step (3) into a methoxylation reagent, and carrying out methoxylation reactions to obtain 4-amino-2,6-dimethoxyl pyrimidine. The synthesis method adopts a novel synthesis route, which will not generate a large amount of phosphorus containing wastewater. The provided method is green and environmentally friendly and generates prominent social benefits.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a synthesis method of 4-amino-2.6-dimethoxypyrimidine. Background technique [0002] 4-amino-2.6-dimethoxypyrimidine, CAS number: 3289-50-7, molecular formula: C 6 h 9 N 3 o 2 , Molecular weight: 155.15, white crystal, melting point: 149-152 ° C, is an important intermediate for the synthesis of sulfa drugs sulfadimethoxine. Sulfadimethoxine has very low toxicity and is particularly effective for upper respiratory tract and urinary tract infections. It has very slight irritation to the kidneys, and its concentration in the blood can be maintained for a long time. Therefore, the frequency and dose of administration can be greatly reduced. reduce. Therefore, it is of practical significance to study the synthesis of the drug. [0003] There are two main methods for the synthesis of 4-amino-2,6-dimethoxypyrimidine: [0004] (1) Barbituric acid method, that is, use phosphorus ...

Claims

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Application Information

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IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor 张玉朱林飞王小龙
Owner YANGZHOU TIANHE PHARM CO LTD
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