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Synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine

A synthesis process, 3-D technology, applied in directions such as organic chemistry, can solve problems such as low yield, unfavorable large-scale application, etc., and achieve the effects of increasing total yield, increasing individual yield and reducing cost

Active Publication Date: 2016-01-06
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the above-mentioned prior art discloses a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine, which can meet certain needs, but in the process of realizing the present invention, the inventors found that the above-mentioned prior art scheme still has There are some deficiencies and shortcomings, such as the yield of 4-amino-6-hydroxypyrimidine synthesis step is 85-88%, and the total yield of 4-chloropyrrolo[2,3-D]pyrimidine is 50-58% , the yield is low, which is not conducive to large-scale industrial application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] This embodiment relates to a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine, which consists of the following steps:

[0022] Step 1, dissolve 20g of ethyl cyanoacetate and thiourea in ethanol at a molar ratio of 1:2, slowly add sodium ethoxide at 2°C, the molar ratio of ethyl cyanoacetate to sodium ethoxide is 1:2, stir at room temperature for 1.5 hour, then warming up to 90°C, reflux reaction for 9 hours, cooling to room temperature, filtering, washing the solid with 30ml ethanol, and drying at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 85%;

[0023] Step 2, adding the above-mentioned 2-mercapto-4-amino-6-hydroxypyrimidine to ammonia water, the mass ratio of 2-mercapto-4-amino-6-hydroxypyrimidine to ammonia water is 1:15, and the mass concentration of ammonia water is 25 %, then add active nickel and titanium dioxide, the molar ratio of 2-mercapto-4-amino-6-hydroxypyrimidine, active nickel and titanium dioxide is 1:4:1.5, heat to 90°C,...

Embodiment 2

[0028] This embodiment relates to a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine, which consists of the following steps:

[0029] Step 1: Dissolve 20 g of ethyl cyanoacetate and thiourea in ethanol at a molar ratio of 1:1, slowly add sodium ethoxide at 3°C, the molar ratio of ethyl cyanoacetate to sodium ethoxide is 1:3, and stir at room temperature for 1 hour, then warming up to 90°C, reflux reaction for 10 hours, cooling to room temperature, filtering, washing the solid with 30ml of ethanol, and drying at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 83%;

[0030] Step 2, adding the above-mentioned 2-mercapto-4-amino-6-hydroxypyrimidine to ammonia water, the mass ratio of 2-mercapto-4-amino-6-hydroxypyrimidine to ammonia water is 1:10, and the mass concentration of ammonia water is 25 %, then add active nickel and titanium dioxide, the molar ratio of 2-mercapto-4-amino-6-hydroxypyrimidine, active nickel and titanium dioxide is 1:5:0.7, heat t...

Embodiment 3

[0035]This embodiment relates to a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine, which consists of the following steps:

[0036] Step 1, dissolve 20g of ethyl cyanoacetate and thiourea in ethanol at a molar ratio of 1:2, slowly add sodium ethoxide at 5°C, the molar ratio of ethyl cyanoacetate to sodium ethoxide is 1:1.5, stir at room temperature for 1.5 hours, then heated up to 100°C, refluxed for 8 hours, cooled to room temperature, filtered, the solid was washed with 30ml of ethanol, and dried at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 82%;

[0037] Step 2, the above-mentioned 2-mercapto-4-amino-6-hydroxypyrimidine is added to ammonia water, the mass ratio of 2-mercapto-4-amino-6-hydroxypyrimidine to ammonia water is 1:15, and the mass concentration of ammonia water is 30 %, then add active nickel and titanium dioxide, the molar ratio of 2-mercapto-4-amino-6-hydroxypyrimidine, active nickel and titanium dioxide is 1:3:1.0, heat to 80°C,...

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Abstract

The invention relates to a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine. The synthesis process comprises the step of sequentially synthesizing 2-sulfydryl-4-amino-6-hydroxypyrimidine, 4-amino-6-hydroxypyrimidine, 4-hydroxypyrrolo[2,3-D]pyrimidine and 4-chloropyrrolo[2,3-D]pyrimidine through four-step reaction by taking ethyl cyanoacetate, thiourea, sodium ethoxide, 2-chloroacetaldehyde and sodium acetate as raw materials, ethanol, ammonia water, water and phosphorus oxychloride as solvents as well as active nickel and titanium dioxide as catalysts to obtain a target product, namely 4-chloropyrrolo[2,3-D]pyrimidine. According to the synthesis process, the cheap and available titanium dioxide is additionally provided in the second step and is used as the catalyst, so that the yield of 4-amino-6-hydroxypyrimidine serving as an intermediate product in the second step is remarkably increased, furthermore, the total yield of 4-chloropyrrolo[2,3-D]pyrimidine is increased, the cost is effectively reduced, and the synthesis process is suitable for large-scale industrial synthesis application.

Description

technical field [0001] The invention relates to a synthesis process of pyrrolopyrimidine compounds, in particular to a synthesis process of 4-chloropyrrolo[2,3-D]pyrimidine. Background technique [0002] 4-Chloropyrrolo[2,3-D]pyrimidine is an important raw material for the synthesis of many antibacterial drugs, antineoplastic drugs, and antipyrrotomal drugs, and is widely used in the field of medicine. Therefore, it is of great significance and application value to study the synthetic technology of 4-chloropyrrolo[2,3-D]pyrimidine. [0003] CN101830904A (publication date 2010.09.15) discloses a preparation method of 4-chloropyrrolopyrimidine, which uses ethyl cyanoacetate, thiourea, sodium ethylate, 2-chloroacetaldehyde and sodium acetate as raw materials, and ethanol, Ammonia, water and phosphorus oxychloride as solvent, active nickel as catalyst, through the synthesis of 2-mercapto-4-amino-6-hydroxypyrimidine, the synthesis of 4-amino-6-hydroxypyrimidine, the synthesis of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 谢应波张庆张华徐肖冰罗桂云
Owner 上海泰坦科技股份有限公司
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