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6-aryl aminopyrimidine compound and synthetic method thereof

An arylaminopyrimidine and a synthesis method technology are applied in the field of 6-arylaminopyrimidine compounds and their synthesis, which can solve the problems of low efficiency, inability to meet high-throughput screening, difficulty in compound synthesis, and the like, and achieve high yield , to achieve the effect of molecular diversity and product stability

Inactive Publication Date: 2008-11-12
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition to replacing traditional organic solvents and reducing pollution, solvent-free reactions also provide a new medium environment for reaction molecules, thereby changing and improving the conversion rate of the reaction, and making it easier to carry out separation and purification processes, etc.; On the other hand, due to the low efficiency of traditional synthetic methods, it is difficult to achieve the synthesis of a large number of compounds, which is far from meeting the requirements of high-throughput screening and drug research and development.

Method used

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  • 6-aryl aminopyrimidine compound and synthetic method thereof
  • 6-aryl aminopyrimidine compound and synthetic method thereof
  • 6-aryl aminopyrimidine compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Synthesis of 2-amino-6-p-chlorophenyl-4-methylthiopyrimidine (A): 5.1 grams of dry 1-p-chlorophenyl-3,3-dimethylsulfanyl was added successively in a 250 ml round-bottomed flask -Acrylone crystals, 14.4 grams of dry guanidine carbonate crystals, heated to 115° C. in an oil bath under stirring with a magnetic stirrer, reacted for 4 hours and the mixture turned into a yellow powder, and the TLC spot plate detection reaction was complete, and the reaction was stopped, and the resulting yellow powder was Washed twice with 50 ml of hot water, filtered while hot, and dried naturally, yield 98%, melting point: 140°C-141°C. 1 H NMR (500MHz, CDCl 3 )δppm: 2.54 (3H, S-CH 3 ), 5.29 (2H, NH2); 13 C NMR (125MHz, CDCl 3 )δppm: 12.8, 77.4, 129.3, 162.5, 172.4. ESI-MS for C 11 h 10 ClN 3 S Calcd.251.0362 (M + ); Found: 252.0503(M + +H).

Embodiment 2

[0061] Synthesis of 2-amino-6-phenyl-4-methylthiopyrimidine (B): 5.55 g of dry 1-phenyl-3,3-dimethylthio-propenone were successively added to a 250 ml round bottom flask Crystals, 14.4 grams of dry guanidine carbonate crystals were heated to 115° C. with an oil bath under magnetic stirrer stirring, and the mixture became a yellow powder after 4 hours of reaction. The TLC spot plate detection reaction was complete, and the reaction was stopped. The resulting yellow powder was mixed with 50 ml Washing with hot water twice, suction filtration while hot, air-drying, the yield is 90%, melting point: 114°C-115°C. 1 H NMR (500MHz, CDCl 3 )δppm: 2.46 (3H, S-CH 3 ), 4.98 (2H, NH2); 13 C NMR (125MHz, CDCl 3 )δppm: 12.8, 77.4, 129.0, 162.8, 172.1. ESI-MS for C 11 h 11 N 3 S Calcd.217.0674 (M + ); Found: 218.0881(M + +H).

Embodiment 3

[0063] Synthesis of 2-amino-6-p-methylphenyl-4-methylthiopyrimidine (D): 5.1 grams of dry 1-p-methylphenyl-3,3-di Methylthio-propenone crystals, 14.0 grams of dry guanidine carbonate crystals, heated to 115° C. with an oil bath under stirring with a magnetic stirrer, reacted for 4 hours and the mixture turned into a yellow powder, and the TLC spot plate detection reaction was complete, and the reaction was stopped. The obtained yellow powder was washed twice with 50 milliliters of hot water, suction filtered while it was hot, and dried naturally, with a yield of 82%.

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Abstract

The invention discloses novel 6-aryl amino pyridines and a method for synthesizing the same. The synthetic method takes singly substituted dialkyl sulfide (II), guanidinium (III)or thiourea (IV) and amine as raw materials, uses nonsolvent method or multicomponent reaction, and synthesizes the 6-aryl amino pyridines with lateral reactivity in formula (I) simply and high efficiently with high yield. The synthetic method has the characteristics of simple course, environment-friendly method and high yield.

Description

technical field [0001] The present invention relates to a 6-arylaminopyrimidine compound (I) with potential pharmaceutical activity and a synthesis method thereof. Background technique [0002] Aminopyrimidines have outstanding biological activities, such as anti-HIV-1 reverse transcriptase, dihydrofolate reductase, anti-tumor, protein kinase, bacteria, fungi and other activities; aminopyrimidines have excellent physiological activities such as: TMC120, R185545, TMC125 (Das, K.; Clark, A.D., Jr.; Lewi, P.J.; et al. J. Med. Chem. 2004, 47, 2550-2560) etc. are non-nucleoside reverse transcriptase inhibitors, which are effective in the treatment of human immune The use of AIDS (AIDS) caused by deficient virus (HIV) has attracted much attention because of its high efficiency, low toxicity, and high selectivity. However, the virus quickly develops resistance and cross-resistance to this class of drugs (Deeks , S.G.J.Acquired Immune Defic.Syndr.2001, 26, S25), the curative effect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47A61P31/18A61P35/00
Inventor 林军刘永江严胜骄牛延菲郑晗黄荣
Owner YUNNAN UNIV