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2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof

A technology of pyrimidine derivatives and synthesis methods, applied in the field of 2H-pyrazolo[3,4-d]pyrimidine derivatives and synthesis

Inactive Publication Date: 2011-07-06
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure and synthesis method of this type of compound have not been reported before

Method used

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  • 2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof
  • 2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof
  • 2H-pyrazolo [3, 4-d] pyrimidine derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2-phenyl-4-chophoprazole and [3,4-D] pyrimidine (3A)

[0018]

[0019] Add 50ml of THF, 5.0mmol benzaline hydrochloride and 5.0 mmol triamine at a 100ml three-port boil bottle, stir at room temperature for 1h, slowly dripping 5.0 mmol 4,6-dichloropatidine -5-formaldehyde under the protection of nitrogen, drippingAdd 11.0mmol triominerine after completion, continue to react at room temperature, TLC tracking (expanded agent v 丙酮 : V 石油醚 = 1: 2), the reaction ends after 25H, the concentrated solvent of decompression and distillation to 10ml, add 20ml of water, have a large amount of white solid, cool to room temperature filtration, filter the residue to be separated by methanol, silicone column layer analysis (V v 丙酮 : V 石油醚 = 1: 2).

Embodiment 2

[0021] 2- (4-bromopenezyl) -4-chloro-2H-pyrazole and [3,4-D] pyrimidine (3B)

[0022]

[0023] Add 60ml of THF to 100ml of three-mouth bottle, 5.0 mmol 4-bromybenzine hydrochloride and 5.5 mmol trivial. The room temperature is stirred for 1h, and the nitrogen is slowly dripped with 5.5mmol 4,6-dichloropatidine -5--------Formaldehyde, add 12mmol triple anlamine after dripping, continue to react at room temperature, TLC tracking (unfolding agent v 丙酮 : V 石油醚 = 1: 2), after 32H, the reaction ends, decompression and distillation of concentrated solvents to 10ml, add 20ml of water, a large amount of brown -yellow solid precipitation, cooling to room temperature filtration, filtering residue with methanol to crystallize, silicone column layer analysis (V v 丙酮 : V 石油醚 = 1: 2).

Embodiment 3

[0025] 2- (4-chlorophenyl) -4-chloro-2H-pyrazole and [3,4-D] pyrimidine (3C)

[0026]

[0027] Add 50ml of THF to 100ml of three-mouth bottle, 5.0 mmol 4-chlorophenhebenate hydrochloride and 6.3mmol trivial. Stir at room temperature for 1h, slowly dripping 6.0mmol 4,6-dichloropatidine -5- under nitrogen protection.Formaldehyde, add 13mmol triple anlamine after dripping, continue to react at room temperature, TLC tracking (expander V 丙酮 : V 石油醚 = 1: 2), the reaction ends after 28h, the concentrated solvent of decompression distillation is 10ml, adding 20ml water, a large amount of yellow solid precipitation, cooling to room temperature filtration, filtering slag with methanol heavy crystals, silicone column layer analysis (V v 丙酮 : V 石油醚 = 1: 2).

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Abstract

The invention belongs to the field of organic synthesis and relates to a 2H-pyrazolo [3, 4-d] pyrimidine derivative (i.e., 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine) and a synthetic method thereof. In the general structural formula of 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine, R refers to hydrogen, alkyl, alkoxyl, halogen, cyan, nitro, carboxyl, ester group and the like; and tetrahydrofuran is adopts as solvent, 4-substituted phenylhydrazine reacts with 4, 6-(dichloro-pyrimidine)-5-methanal under the action of triethylamine, most solvent is vaporized after reaction completion, a crude product precipitates out as a solid by adding water, the crude product filtered out is recrystallized with absolute methanol, and then isomer is removed by a column separation method to obtain corresponding 2-(4-substituted phenyl)-4-chloro-2H-pyrazolo [3, 4-d] pyrimidine. The 2H-pyrazolo [3, 4-d] pyrimidine derivative is synthesized for the first time by selecting reasonable reaction conditions.

Description

Technical field [0001] The present invention involves a 2H-pyrazole and [3,4-D] pyrimidine derivatives, namely 2- (4-replace the phenyl) -4-clotic-2H-pyrazoleThe synthetic method is to replace the phenylhol and 4,6-dichloropyamine -5-formaldehyde as the raw material, and the tetrahydrocarbufu as the solvent.Azoli [3,4-D] pyrimidine. Background technique [0002] As an important biomolecular DNA and ATP structure unit, pyrazole and its pyrazole derivatives have a wide range of biological activity. They are the advantage structure in the design of new drugs and have been highly valued by drug chemical workers.At present, many anti-cancer drugs have been developed based on 1H-pyrazole [3,4-D] pyrimidine derivatives.treat.For example, allopurinol, which has been used for clinical, can treat primary and secondary hyperuricemia, repeated attacks or chronic gout, gout, uric acid renal, and uric acid nephropathy, and high uric acid and bloodMany other pyrine derivatives have also been pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 孟启周长青陈海浪姜艳孙小强
Owner CHANGZHOU UNIV
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