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Preparation method of (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone

An aryl ketone and pyrazoline technology, applied in the field of preparation of aryl ketones, can solve problems such as being unsuitable for industrial scale-up production and industrial application, difficult separation and purification of products, harsh reaction conditions, etc. The effect of easy product and few side reactions

Inactive Publication Date: 2020-06-19
CHENGDU CHEMPARTNER
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved by this invention is that the preparation method of (4-chloro-1H-pyrazoline [3,4-d] pyrimidin-3-yl) aryl ketone in the prior art has long reaction route and poor selectivity. There are many reactions, the product is extremely difficult to separate and purify, the yield is low, the reaction conditions are harsh and the safety is poor, and it is not suitable for industrial scale-up production and industrial application

Method used

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  • Preparation method of (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone
  • Preparation method of (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone
  • Preparation method of (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone

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Embodiment 1

[0047] The synthesis of embodiment 1,4-chloro-1H-pyrazoline [3,4-d] pyrimidin-3-yl) (o-tolyl) ketone

[0048]

[0049] A solution of A-1 (2.0g) in tetrahydrofuran (20mL) was cooled to -78°C with stirring under nitrogen protection, and n-butyllithium (8mL) was slowly added dropwise, and compound A-2a (1.6g) was added dropwise after stirring for 30 minutes Tetrahydrofuran (10mL) solution was maintained at -78°C for 30 minutes and stirred for 30 minutes, then naturally rose to room temperature and continued to stir for 2 hours; after the reaction was completed, the reaction system was extracted with water (50mL) and extracted with ethyl acetate, and the organic phase was collected to saturate Washed with salt water, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to remove the solvent, and the residue was separated and purified by column chromatography to obtain the white solid target product compound (4-chloro-1H-pyrazoline[3,4-d]pyrimidine-3- bas...

Embodiment 2

[0053] Embodiment 2, the synthesis of (4-chloro-1H-pyrazoline [3,4-d] pyrimidin-3-yl) (2-chloro-4-phenoxyphenyl) ketone

[0054]

[0055] A solution of A-1 (2.0g) in tetrahydrofuran (20mL) was stirred and cooled to -78°C under nitrogen protection, and n-butyllithium (8mL) was slowly added dropwise, and compound A-2b (2.5g) was added dropwise after stirring for 30 minutes Tetrahydrofuran (15mL) solution was maintained at -78°C and stirred for 60 minutes, then naturally rose to room temperature and continued to stir for 3 hours; after the reaction was completed, the reaction system was extracted with water (50mL) and extracted with ethyl acetate, and the organic phase was collected to saturate Washed with salt water, dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated to remove the solvent, and the residue was separated and purified by column chromatography to obtain the white solid target product compound (4-chloro-1H-pyrazoline[3,4-d]pyrimidine-3- b...

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Abstract

The invention provides a preparation method of (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone. With 3-bromo-4-chloro-1H-pyrazoline [3, 4-d] pyrimidine as a raw material, the target product compound (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone (formula A) is prepared through one-step condensation with an acyl chloride compound. The preparation method of the (4-chloro-1H-pyrazoline [3, 4-d] pyrimidine-3-yl) aryl ketone is short in reaction route, few in side reactions and easy in product purification, the yield of the whole synthesis route is increased, and large-scale production and industrial popularization are facilitated.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, and more specifically, to a preparation method of (4-chloro-1H-pyrazoline[3,4-d]pyrimidin-3-yl)aryl ketone. Background technique [0002] (4-Chloro-1H-pyrazoline[3,4-d]pyrimidin-3-yl)aryl ketone, active core pyrimidine ring and pyrazoline ring, contains multiple nitrogen heteroatoms, is a synthetic It is an important intermediate compound of new medical drug compounds containing nitrogen heteroatoms or containing pyrimidine ring and pyrazoline ring. The structure of (4-chloro-1H-pyrazoline [3,4-d] pyrimidin-3-yl) aryl ketone is shown in the following formula: [0003] [0004] After searching the prior art, there is no report on the preparation method of the above-mentioned (4-chloro-1H-pyrazoline [3,4-d] pyrimidin-3-yl) aryl ketone; the prior art discloses the synthesis of pyrazole Phylinopyrimidine fused ring compounds are generally prepared by ring-closing methods, whic...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 仵清春姜志成
Owner CHENGDU CHEMPARTNER
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