Preparation method of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine

A methylpyridine, 3-d technology, applied in the field of pharmaceutical preparation, can solve the problems of unsuitability for industrial production, poor product purity, etc., and achieve the effects of high yield, few by-products, and easy operation

Inactive Publication Date: 2016-09-21
国药集团容生制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology involves making certain substances that are used in medicine or chemicals with specific properties such as reducing blood pressure without causing other side effects like heart attacks or strokes. These new compounds can be made through reaction between different bases (NaOH), alcohols, amines, etc.) at room temperature under acidic conditions over time.

Problems solved by technology

This patented technical problem addressed in the patents describes how to efficiently manufacture tafatinib citric acid salt used alone as an antiinflammator drug called etanercept.

Method used

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  • Preparation method of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine
  • Preparation method of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine
  • Preparation method of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine

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Effect test

Embodiment 1

[0027] Put 11.0 g of sodium hydroxide and 450 mL of methanol into the reaction flask, and stir for 1 h. Add N-((3R,4R)-1-benzyl-4-methylpyridin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine- 45.0 g of 4-amine was heated to 40°C and stirred for 4 h. The reaction was stirred, cooled to 8°C, 450 mL of water was added dropwise, and filtered to obtain 29.6 g of a white solid with a yield of 96.0%.

Embodiment 2

[0029] Put 10.0 g of sodium hydroxide and 450 mL of methanol into the reaction flask, and stir for 2 h. Add N-((3R,4R)-1-benzyl-4-methylpyridin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine- 4-amine 55.0 g, heated to 50 ° C, stirred for 6 hours. The reaction was stirred and cooled to 5°C, 450 mL of water was added dropwise, and filtered to obtain a white solid.

Embodiment 3

[0031] Put 10.0 g of sodium hydroxide and 450 mL of methanol into the reaction flask, and stir for 1.5 h. Add N-((3R,4R)-1-benzyl-4-methylpyridin-3-yl)-N-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine- 4-amine 50.0 g, heated to 50 ° C, stirred for 8 h. The reaction was stirred and cooled to 10°C, 900 mL of water was added dropwise, and filtered to obtain a white solid.

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Abstract

The invention discloses a preparation method of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine. The method takes sodium hydroxide as alkali and methyl alcohol as a solvent, and the intermediate N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine is obtained in a reaction of N-((3R, 4R)-1-benzyl-4-methyl pyridine-3-yl)-N-methyl-7-toluenesulfonyl-7H-pyrrolo-[2, 3-d] pyrimidine-4-amine. The method is high in yield, fewer in by-products and simple and convenient to operate, thus being both suitable for small-scale laboratory preparation and large-scale industrial production.

Description

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Claims

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Application Information

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Owner 国药集团容生制药有限公司
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