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Preparation method of 5-[(3, 4, 5-trimethoxyphenyl)-methyl]-2, 4-pyrimidine diamine

A technology of trimethoxyphenyl and trimethoxybenzaldehyde, which is applied in the field of preparation of 5-[-methyl]-2,4-pyrimidinediamine, can solve the problems of environmental protection and safety risks, difficult recovery of DMSO, and synthesis There are many reaction steps, etc., to achieve the effect of reducing the generation of solid waste, no impact on purity, and reducing equipment costs

Inactive Publication Date: 2021-03-12
SHOUGUANG FUKANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Due to the many steps of the synthesis reaction and the complex process, catalysts such as zinc chloride and potassium tert-butoxide were added in addition to DMSO during the synthesis process, which not only greatly increased the cost of the product, but also produced a large amount of solid waste, and caused In addition to the difficulty of recycling DMSO, there is a huge safety risk in the recycling process
[0008] Many researchers have successively improved the synthetic route of this compound, but still have not replaced DMSO, there are problems such as high cost and low yield, and environmental protection and safety risks still exist

Method used

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  • Preparation method of 5-[(3, 4, 5-trimethoxyphenyl)-methyl]-2, 4-pyrimidine diamine
  • Preparation method of 5-[(3, 4, 5-trimethoxyphenyl)-methyl]-2, 4-pyrimidine diamine

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Experimental program
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Effect test

Embodiment 1

[0026] In a 1000mL four-necked flask equipped with mechanical stirring, add 21.3g of acrylonitrile and 37.4g of aniline into the flask and stir, then add 70.0g of methanol and 17.2g of sodium methoxide into the flask and stir until dissolved. Add 3,4,5-trimethoxybenzaldehyde crude product 75.0g,

[0027] After the addition was completed, the temperature was raised to reflux for 2 hours, followed by TLC until the spots of the TMB raw material disappeared. After the reaction, the temperature was cooled to 1°C, and stirred for 1 hour. After suction filtration, the filter cake was dried at 80°C to obtain 115.3 g of dry solids. 93%, purity ≥99.8%.

Embodiment 2

[0029] In a 1000mL four-neck flask equipped with mechanical stirring, add 21.3g of acrylonitrile and 37.4g of aniline into the flask and stir, then add 70.0g of methanol and 17.2g of sodium methoxide into the flask and stir until dissolved. Add 3,4,5-trimethoxybenzaldehyde crude product 75.0g,

[0030] After the addition was completed, the temperature was raised to reflux for 2.5 hours, followed by TLC until the spots of the TMB raw material disappeared. After the reaction was completed, the temperature was cooled to 3°C, and stirred for 1.2 hours. After suction filtration, the filter cake was dried at 85°C to obtain 116.5 g of dry solids. The yield is 94%, and the purity is ≥99.9%.

Embodiment 3

[0032] In a 1000mL four-neck flask equipped with mechanical stirring, add 21.3g of acrylonitrile and 37.4g of aniline into the flask and stir, then add 70.0g of methanol and 17.2g of sodium methoxide into the flask and stir until dissolved. Add 3,4,5-trimethoxybenzaldehyde crude product 75.0g,

[0033] After the addition was completed, the temperature was raised to reflux for 3 hours, followed by TLC until the spots of the TMB raw material disappeared. After the reaction, the temperature was cooled to 5°C, and stirred for 1.4 hours. After suction filtration, the filter cake was dried at 90°C to obtain 116.8 g of dry solids. The rate is 94%, and the purity is ≥99.9%.

[0034] Unless otherwise specified, the percentages used in the present invention are all mass percentages.

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Abstract

The invention provides a preparation method of 5-[(3, 4, 5-trimethoxyphenyl) methyl]-2, 4-pyrimidine diamine, and the method comprises the following steps: performing stirring and dissolving, performing heating and refluxing, performing stirring and performing suction filtration. In the stirring and dissolving step, acrylonitrile, aniline, methanol and sodium methoxide are added into a four-neck flask with a mechanical stirrer and stirred to be dissolved; the heating reflux comprises the following steps: adding a 3, 4, 5-trimethoxybenzaldehyde crude product at 50-60 DEG C within 20-30 minutes,heating to reflux and react for 2-3 hours, and carrying out TLC tracking until spots of the TMB raw material disappear. The invention has the beneficial effects that the cost is saved, the generationof solid wastes is reduced, the safety of the production process is improved, the equipment cost is reduced, and the safety risk is avoided; the yield can be increased to 93%; the method can be directly used for the next synthesis without refining, and has no influence on the purity of trimethoprim, thereby lowering the production cost and the like.

Description

technical field [0001] The invention relates to the technical field of bacteriostat preparation, in particular to a preparation method of 5-[(3,4,5-trimethoxyphenyl)-methyl]-2,4-pyrimidinediamine. Background technique [0002] 5-[(3,4,5-trimethoxyphenyl)-methyl]-2,4-pyrimidinediamine, also known as trimethoprim (TMP for short), also known as synergistic sulfonamide, is a Class lipophilic weakly basic pyrimidine bacteriostatic agent, the structural formula of trimethoprim is as follows: [0003] [0004] Trimethoprim is a light skin antibacterial agent. Its antibacterial spectrum is similar to that of sulfa drugs, but its antibacterial effect is stronger. It is effective against E. It is widely used in the treatment of urinary tract infection, intestinal infection, respiratory infection, bacillary dysentery, enteritis, typhoid fever, meningitis, otitis media, meningitis, sepsis and soft tissue infection. [0005] At present, there are many studies on trimethoprim. Accord...

Claims

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Application Information

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IPC IPC(8): C07D239/49
CPCC07D239/49
Inventor 国建辉刘累累朱素美李润泉
Owner SHOUGUANG FUKANG PHARMA
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