Pharmaceutical intermediate pyridine[2,3-d]pyrimidine-4(3H)-ketone and preparation thereof

A 3-d, pyrimidine technology, applied in the field of synthesis of drug intermediate pyridin[2,3-d]pyrimidin-4-one, to achieve the effect of simple operation, good biological activity and fast response

Inactive Publication Date: 2011-03-16
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when preparing these alkylated pyrimidine derivatives, highly toxic halogenated hydrocarbons or dimethyl sulfate are used, and toxic organic solvents (such as DMF, DMSO and methanol, etc.) need to be dissolved in the presence of a strong base. ) for a longer reaction time

Method used

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  • Pharmaceutical intermediate pyridine[2,3-d]pyrimidine-4(3H)-ketone and preparation thereof
  • Pharmaceutical intermediate pyridine[2,3-d]pyrimidine-4(3H)-ketone and preparation thereof
  • Pharmaceutical intermediate pyridine[2,3-d]pyrimidine-4(3H)-ketone and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1, 2-methyl-5, 7-two phenylpyamine [2,3-d ] Piopidine-4 ( 3H ) -Fone preparation

[0030] (1) 2-cymbal-5,7-two phenylpyamine [2,3- d ] Piopidine-4 ( 3H ) -Fone preparation

[0031] 1 mmol 2-amino-3-methyl amino-4,6-two phenylpyridine, 2 mmol CS 2 , 3 mmol koh, 2 ml dmf adds to a 10 mL sealing tube of magnetic stirring.Set the microwave radiation power of 10 W, the temperature rises from room temperature to 150 ° C, and continues to radiate 15 min.After TLC detection, after the reaction stops, the reaction solution is cooled to room temperature, adds 5 ml of water, a large amount of solids are precipitated, filtering, and the ethanol-DMF heavy crystal obtains the product.The income rate is 81%.

[0032] through 1 Hnmr, 13 CNMR, FT-IR, Anal. Calcd detection, its products are pure products.Its performance indicators or characteristic data are as follows: 1 H nmr (400 mHz, DMSO- d 6 Cure δ 13.20 (br, 1H), 12.40 (br, 1H), 8.24 (D, D, J = 6.4 Hz, 2H), 7.65-7.43 (m, 9H). 1...

Embodiment 2

[0038] Implementation of 2, 2-methyl-5- (4-chlorophenyl) -7-phenylpyridine [2,3- d ] Piopidine-4 ( 3H ) -Fone preparation

[0039] (1) 2-cymbal-5- (4-chlorophenyl) -7-phenyl pyridine [2,3- d ] Piopidine-4 ( 3H ) -Fone preparation

[0040] 1 mmol 2-amino-3-methyl amin amino-4- (4-chlorophenyl) -6-phenylpyamine, 2 mmol CS 2 , 3 mmol koh, 2 ml dmf adds to a 10 mL sealing tube of magnetic stirring.Set the microwave radiation power of 10 W, the temperature rises from room temperature to 150 ° C, and continues to radiate 15 min.After TLC detection, after the reaction stops, the reaction solution is cooled to room temperature, adds 5 ml of water, a large amount of solids are precipitated, filtering, and the ethanol-DMF heavy crystal obtains the product.The income rate is 88%.

[0041] through 1 Hnmr, 13 CNMR, FT-IR, Anal. Calcd detection, its products are pure products.Its performance indicators or characteristic data are as follows:

[0042] 1 H nmr (400 mHz, DMSO- d 6 Cure δ 13.14 (br,...

Embodiment 3

[0048] Example 3, 2-methyl-5- (4-methyl-phenyl) -7-phenyl pyridine [2,3- d ] Piopidine-4 ( 3H ) -Fone preparation

[0049] (1) 2-cymbal-5- (4-methyl-phenyl) -7-phenyl pyridine [2,3- d ] Piopidine-4 (3H ) -Fone preparation

[0050] 1 mmol 2-amino-3-methyl amin amino-4- (4-methyl-phenyl) -6-phenylpyridine, 2 mmol CS 2 , 3 mmol koh, 2 ml dmf adds to a 10 mL sealing tube of magnetic stirring.Set the microwave radiation power of 10 W, the temperature rises from room temperature to 150 ° C, and continues to radiate 15 min.After TLC detection, after the reaction stops, the reaction solution is cooled to room temperature, adds 5 ml of water, a large amount of solids are precipitated, filtering, and the ethanol-DMF heavy crystal obtains the product.The income rate is 93%.

[0051] through 1 Hnmr, 13 CNMR, FT-IR, Anal. Calcd detection, its products are pure products.Its performance indicators or characteristic data are as follows:

[0052] 1 H nmr (400 mHz, DMSO- d 6 Cure δ 13.09 (br, 1H), ...

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Abstract

The invention provides a new pharmaceutical intermediate pyridine[2,3-d]pyrimidine-4(3H)-ketone, which belongs to the technical field of chemical synthesis. The pyridine[2,3-d]pyrimidine-4(3H)-ketone is successfully synthesized by performing focused microwave radiation on 2-sulfydryl-5,7-diarylpyridine[2,3-d]pyrimidine-4(3H)-ketone by taking dimethyl carbonate (DMC) as a methylation agent, MgO as a catalyst, DMSO as a promoter and tetrabutyl ammonium bromide as an oxidant. Experiments demonstrate that pyridine[2,3-d]pyrimidine-4(3H)-ketone has broad-spectrum bioactivity and shows high bioactivity particularly in terms of sterilization, inflammation diminishment, gout resistance, stimulant resistance, folic acid resistance, virus resistance and the like. In the synthesis process of the invention, DMC participates in the reaction as a reactant and also serves as a solvent of the reaction without other organic solvents, thereby saving the cost and being conducive to environmental protection. The invention has relatively good application prospect.

Description

Technical field [0001] The invention is a chemical synthesis technology field, involving a new drug intermediate pyridine [2,3- d ] Piopidine-4 ( 3H )--Synthesis method of ketone. Background technique [0002] Single-based or di metrophic pyrine-2- (sulfur) ketone compounds have good calcium antagonistic activity, and they are also synthesis N3 The key intermediates of pyrine derivatives such as alkyl -based / l -based, occupy more important positions in synthesis and natural products containing pyrine.There are not many literature methods for using pyrine to prepare alkyl -based pyrine derivatives, which mainly include the reaction of pyrine and alkyl halide or sulfate dihydride in the existence of alkaline reagents.Atwal's improved Biginelli reaction to prepare alkylraine derivatives.However, when preparing these alkylraidine derivatives, the toxic hydrocarbon or sulfate is used, and it is necessary to exist to a toxic organic solvent (such as DMF, DMSO, methanol, etc.) The reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 王喜存梁军灵权正军姬鹏燕杨国俊
Owner NORTHWEST NORMAL UNIVERSITY
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