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Synthetic process of 4‑chloropyrrolo[2,3‑d]pyrimidine

A synthetic process, the technology of chloropyrrole, which is applied in the direction of organic chemistry, can solve the problems of unfavorable large-scale application and low yield, and achieve the effect of increasing the individual yield, increasing the total yield, and reducing costs

Active Publication Date: 2017-12-15
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 is still There are some deficiencies and shortcomings, such as the yield of 4-amino-6-hydroxypyrimidine synthesis step is 85-88%, 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 20 g of ethyl cyanoacetate and thiourea in ethanol at a molar ratio of 1:2, and slowly add sodium ethoxide at 2°C. The molar ratio of ethyl cyanoacetate to sodium ethoxide is 1:2, and stir at room temperature for 1.5 After hours, the temperature was raised to 90°C, the reaction was refluxed for 9 hours, cooled to room temperature, filtered, the solid was washed with 30ml ethanol, and dried at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 85%;

[0023] Step two, add the above 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...

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, and 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 After hours, the temperature was raised to 90°C, the reaction was refluxed for 10 hours, cooled to room temperature, filtered, the solid was washed with 30ml ethanol, and dried at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 83%;

[0030] Step 2: Add 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 dioxi...

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 20 g 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, and stir at room temperature for 1.5 After hours, the temperature was raised to 100°C, the reaction was refluxed for 8 hours, cooled to room temperature, filtered, the solid was washed with 30ml ethanol, and dried at 40°C to obtain 2-mercapto-4-amino-6-hydroxypyrimidine with a yield of 82%;

[0037] Step 2: Add the above 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 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:...

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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, anti-tumor drugs, and anti-vertebral worm drugs, and is widely used in the field of medicine. Therefore, the research on the synthesis process of 4-chloropyrrolo[2,3-d]pyrimidine has important significance and application value. [0003] CN101830904A (published date 2010.09.15) discloses a method for preparing 4-chloropyrrolopyrimidine, which uses ethyl cyanoacetate, thiourea, sodium ethoxide, 2-chloroacetaldehyde and sodium acetate as raw materials, and uses ethanol, Ammonia, water and phosphorus oxychloride as solvents, active nickel as a catalyst, through the synthesis of 2-mercapto-4-amino-6-hydroxypyrimidine, 4-amino-6-hydroxypyrimidine, 4-hydroxypyrrolopyrimidine The...

Claims

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Application Information

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Patent Type & Authority Patents(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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