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Method for synthesizing bromophenyl pyrazolo[3,4-d]pyrimidine derivative

A pyrazolo and bromophenyl technology, which is applied in the field of synthesis of bromophenylpyrazolo[3,4-d]pyrimidine derivatives, can solve the problems of large solvent consumption, complicated operation, low total yield and the like , to achieve the effect of improving the level of cleaning

Active Publication Date: 2014-04-09
溧阳常大技术转移中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional synthesis method uses ethoxymethylenemalononitrile and phenylhydrazine derivatives as raw materials, not only the reaction steps are long, the total yield is not high, and at the same time, due to the influence of isomers, the product purification is difficult, and column Separation technology, complex operation, large solvent consumption, and a large amount of waste liquid that is difficult to handle

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Step 1: Add 50ml of tetrahydrofuran and 5mmol p-bromophenylhydrazine to a 100ml three-necked flask, add 5mmol triethylamine at the same time, stir at room temperature for 0.5h, then slowly add 5mmol 4,6-dichloropyrimidine-5- formaldehyde ， TLC tracking (developing agent V 丙酮 :V 石油醚 =1:2), after about 1 hour, the reaction was completed, and the insoluble matter was removed by filtration, and the filtrate was distilled under reduced pressure to 20ml, and put in the refrigerator to freeze overnight, and crystallized to obtain a bright yellow solid as the condensation product (A), with a yield of 80%.

[0019] Step 2: Add 50ml of tetrahydrofuran to a 100ml three-necked flask, add the above bright yellow solid (A), stir to dissolve, add 10mmol of triethylamine, continue stirring at room temperature for 32h, distill under reduced pressure to concentrate the solution to 10ml, add 20ml of water, A large amount of brown-yellow solids precipitated, and the filtered solids were ...

Embodiment 2

[0021] Step 1: Add 50ml of tetrahydrofuran and 5mmol p-bromophenylhydrazine to a 100ml three-necked flask, add 6mmol triethylamine at the same time, after stirring at room temperature for 0.5h, slowly add 6mmol 4,6-dichloropyrimidine-5- formaldehyde ， TLC tracking (developing agent V 丙酮 :V 石油醚 =1:2), after about 1.5h, the reaction was completed, and the insoluble matter was removed by filtration, and the filtrate was distilled under reduced pressure to 20ml, and put in the refrigerator to freeze overnight, and crystallized to obtain a bright yellow solid as condensation product (A), with a yield of 85%.

[0022] Step 2: Add 50ml of tetrahydrofuran to a 100ml three-necked flask, add the above bright yellow solid (A), stir to dissolve, add 12mmol of triethylamine, continue stirring at room temperature for 30h, distill under reduced pressure to concentrate the solution to 10ml, add 20ml of water, A large amount of brown-yellow solids precipitated, and the filtered solids were r...

Embodiment 3

[0024] Step 1: Add 50ml of tetrahydrofuran and 5mmol of p-bromophenylhydrazine hydrochloride into a 100ml three-necked flask, add 11mmol of triethylamine at the same time, stir at room temperature for 0.5h, then slowly add 5mmol of 4,6-dichloropyrimidine under nitrogen protection -5-Formaldehyde ， TLC tracking (developing agent V 丙酮 :V 石油醚 =1:2), after about 1.5h, the reaction was completed, the insoluble matter was removed by filtration, the filtrate was distilled under reduced pressure to 20ml, and it was frozen in the refrigerator overnight, and a bright yellow solid was crystallized to obtain a condensation product (A), with a yield of 81%.

[0025] Step 2: Add 50ml tetrahydrofuran to a 100ml three-necked flask, add the above bright yellow solid (A), stir to dissolve, add 8mmol triethylamine, continue stirring at room temperature for 27h, distill under reduced pressure to concentrate the solution to 10ml, add 20ml water, A large amount of brown-yellow solids precipitated...

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Abstract

The invention relates to the field of organic synthesis, in particular to a method for synthesizing a bromophenyl pyrazolo[3,4-d]pyrimidine derivative. 1-(4-bromophenyl)-4-chlorine-1H-yrazolo[3,4-d]pyrimidine is synthesized by two steps, and the method comprises the following steps of: performing condensation on 4-bromophenylhydrazine and 4,6-dichloropyrimidine-5-formaldehyde in a solvent of tetrahydrofuran in the presence of triethylamine, and separating and purifying a condensation product; and dissolving the condensation product with tetrahydrofuran again, adding a proper amount of triethylamine, reacting fully at room temperature, evaporating most solvent after the reaction is finished, adding water to separate out a brownish yellow solid crude product, and recrsystallizing the filtered solid with methanol to obtain the 1-(4-bromophenyl)-4-chlorine-1H-yrazolo[3,4-d]pyrimidine, wherein the product content is more than or equal to 97 percent; and the total yield is over 78 percent. The two steps of reactions are performed at room temperature without column separation, so that the cleanliness degree of the synthetic process is improved.

Description

technical field [0001] The present invention relates to the field of organic synthesis, in particular to the synthesis of a bromophenylpyrazolo[3,4-d]pyrimidine derivative namely 1-(4-bromophenyl)-4-chloro-1H-pyrazolo[3 ,4-d] a new method of pyrimidine, using 4-bromophenylhydrazine and 4,6-dichloropyrimidine-5-carbaldehyde as raw materials to synthesize 1-(4-bromophenyl)-4-chloro- 1H-pyrazolo[3,4-d]pyrimidine. Background technique [0002] As the structural units of important biomolecules DNA and ATP, pyrazolopyrimidine derivatives have a wide range of biological activities and are the dominant structures in the design of new drugs, which have always been highly valued by medicinal chemists. At present, many anticancer drugs have been developed based on 1H-pyrazolo[3,4-d]pyrimidine and other pyrimidine derivatives, which are widely used in the treatment of tumors, inflammation, cardiovascular, asthma and neurological diseases. treat. For example, allopurinol, which has be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 孟启陈海浪周长青姜艳孙小强
Owner 溧阳常大技术转移中心有限公司
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