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Preparation methods of N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine and intermediate thereof

A technology of methyl iodide and compounds, which is applied in the field of preparation of pyrimidine derivatives, can solve problems such as waste, low reaction yield, and use restrictions, and achieve the effects of less pollutant discharge, simple product treatment, and reduced dosage

Active Publication Date: 2013-10-23
TIANJIN HESHENG MEDICAL TECH DEV
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  • Claims
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AI Technical Summary

Problems solved by technology

When preparing 2-methylsulfonyl-4-(3-pyridyl)pyrimidine in this way, and continuing to prepare N-(5-nitro-2-methylpyridyl-3-)-4-(3- During pyridyl)-2-pyrimidinamine, due to the low yield of the two-step reaction, the total yield of the reaction is also affected. In addition, a large amount of waste liquid containing iodide ions will be produced after methylation with methyl iodide, such as waste Can cause pollution and waste afterward, if reclaim iodine, existing reclaim iodine process mainly is to add oxidizing agent such as potassium chlorate in the acidified waste liquid containing iodine ion and then oxidize it into iodine simple substance, need to increase the consumption of oxidizing agent in addition, and Potassium chlorate is an explosive dangerous product, and its use is also subject to greater restrictions

Method used

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  • Preparation methods of N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine and intermediate thereof
  • Preparation methods of N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine and intermediate thereof
  • Preparation methods of N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine and intermediate thereof

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preparation example Construction

[0025] The preparation of embodiment 1-embodiment 4 compound IV, formula is as follows

[0026]

[0027] Reaction process:

[0028] Put compound II and NaOH solution as raw materials into the reaction kettle, stir to dissolve, and lower the temperature to about 0°C. Methyl iodide was added dropwise, and after the addition was completed, the reaction was kept warm until the reaction was complete. Use 0.1M hydrochloric acid to adjust the pH to 4-5, cool down to 20°C, add hydrogen peroxide, and control the addition rate so that the temperature of the reaction system does not exceed 50°C. After the addition, keep warm until the reaction is complete. Use 0.1M Na 2 CO 3 Adjust the pH value to 7.5-8, filter, wash the filter cake with water, and dry to obtain compound IV as the product. The product is weighed and the content of compound IV is detected by HPLC.

[0029] HPLC conditions:

[0030] Use octadecylsilane bonded silica gel as the stationary phase; use 0.05mol / L phospha...

Embodiment 5

[0046] The preparation of embodiment 5 compound I

[0047] Take the compound IV prepared by the method of Example 1 as a raw material,

[0048] The preferred process of the step (3) is as follows, adding compound IV and compound V with a molar ratio of 1:1.5 into the reactor, adding DMF with a volume weight ratio of 8 to compound IV, stirring and dissolving, cooling to -10°C, and keeping at Add sodium hydride in batches at this temperature, the molar ratio of added sodium hydride to compound IV is 2:1, keep the temperature at 20-30° C. until the reaction is complete to obtain compound I after adding sodium hydride.

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Abstract

Preparation methods of N-(2-methylpyridyl-5-nitro-3)-4-(3-pyridinyl)pyrimidin-2-amine and an intermediate thereof are characterized in that N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine is prepared through three step reactions by taking 2-sulfydryl-4-(3-pyridinyl)pyrimidine as a raw material; wherein 2-sulfydryl-4-(3-pyridinyl)pyrimidine is subjected to combination of two reactions comprising iodomethane methylation and oxidation by one-pot synthesis to direct synthesize 2-methylsulfonyl-4-(3-pyridinyl)pyrimidine; then the prepared compound 2-methylsulfonyl-4-(3-pyridinyl)pyrimidine by using the above method is reacted with a raw material compound 2-amino-4-nitrotoluene to obtain the product N-(2-methylpyridyl-5-nitro-3-)-4-(3-pyridinyl)pyrimidin-2-amine. The preparation methods have the advantages that no organic solvent is needed to add during the whole process, product processing is simple, yield is high and pollutant discharge is less.

Description

technical field [0001] The invention relates to a preparation method of pyrimidine derivatives. Background technique [0002] A kind of synthetic method of N-(5-nitro-2-methylpyridyl-3-)-4-(3-pyridyl)-2-pyrimidinamine is disclosed in Chinese patent CN1972917B specification embodiment 1, promptly adopts 2-Methyl-3-amino-5-nitropyridine and 2-methylsulfonyl-4-(3-pyridyl)pyrimidine can be prepared by reaction. [0003] [0004] And Chinese patent application CN201110323144.7 also discloses a kind of synthetic method of 2-methylsulfonyl-4-(3-pyridyl)pyrimidine as follows: [0005] [0006] When R is methyl and X is iodine, the synthetic method disclosed in this application is actually a method for preparing 2-methylsulfonyl-4-(3-pyridyl)pyrimidine using methyl iodide as a methylating reagent, The synthetic method of 2-methylsulfonyl-4-(3-pyridyl)pyrimidine is disclosed in Example 1 of the application description, wherein methylation of iodomethane is used to prepare 2-me...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D401/14
Inventor 何磊田东奎陈松
Owner TIANJIN HESHENG MEDICAL TECH DEV
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