Synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine

A synthetic method, 3-D technology, applied in the direction of organic chemistry, etc., to achieve the effect of simple operation, saving production cost and shortening time

Active Publication Date: 2021-04-20
HANGZHOU ALLSINO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for the preparation of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine, so far there are few reports at home and abroad (WO2007092213)

Method used

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  • Synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine
  • Synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine

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Effect test

Embodiment 1

[0034] see figure 1 , this example provides a synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine:

[0035] Under nitrogen protection, compound I (37.6 g, 200 mmol) was dissolved in tetrahydrofuran (188 mL), and the reaction solution was cooled to -10-10°C. Iron acetylacetonate (3.53 g) was added, and 3.0 M methylmagnesium chloride Grignard reagent tetrahydrofuran solution (133 mL) was slowly added dropwise to the reaction solution, and the reaction temperature was controlled at -10 to 10°C during the dropwise addition. After dropping, continue to keep warm for 1 hour. The reaction solution was added dropwise to saturated aqueous ammonium chloride solution (188mL), stirred for 30 minutes, and separated into layers, the aqueous phase was extracted once with tetrahydrofuran (113mL), the organic phases were combined, washed once with saturated brine (114mL), anhydrous sodium sulfate ( 50 g) was dried, filtered, removed to a thick state, stirred at -10 to 0°C for 0.5 hours,...

Embodiment 2

[0040] see figure 1 , this example provides a synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine:

[0041] Under nitrogen protection, compound I (37.6 g, 200 mmol) was dissolved in tetrahydrofuran (188 mL), and the reaction solution was cooled to -10-10°C. Iron acetylacetonate (10.5 g) was added, and 3.0 M methylmagnesium chloride Grignard reagent tetrahydrofuran solution (133 mL) was slowly added dropwise to the reaction solution, and the reaction temperature was controlled at -10 to 10°C during the dropwise addition. After dropping, continue to keep warm for 1 hour. The reaction solution was added dropwise to saturated aqueous ammonium chloride solution (188mL), stirred for 30 minutes, and separated into layers, the aqueous phase was extracted once with tetrahydrofuran (113mL), the organic phases were combined, washed once with saturated brine (114mL), anhydrous sodium sulfate ( 50 g) was dried, filtered, removed to a thick state, stirred at -10 to 0°C for 0.5 hours,...

Embodiment 3

[0044] see figure 1 , this example provides a synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine:

[0045]Under nitrogen protection, compound I (37.6 g, 200 mmol) was dissolved in tetrahydrofuran (188 mL), and the reaction solution was cooled to -10-10°C. Iron acetylacetonate (3.53 g) was added, and 3.0 M methylmagnesium chloride Grignard reagent tetrahydrofuran solution (100 mL) was slowly added dropwise to the reaction solution, and the reaction temperature was controlled at -10 to 10°C during the dropwise addition. After dropping, continue to keep warm for 1 hour. The reaction solution was added dropwise to saturated aqueous ammonium chloride solution (188mL), stirred for 30 minutes, and separated into layers, the aqueous phase was extracted once with tetrahydrofuran (113mL), the organic phases were combined, washed once with saturated brine (114mL), anhydrous sodium sulfate ( 50 g) was dried, filtered, removed to a thick state, stirred at -10 to 0°C for 0.5 hours, ...

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Abstract

The invention provides a synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine, wherein the comprises the following steps: (a) reacting a substance represented by a formula (I) with a methyl Grignard reagent under the action of a catalyst to obtain a compound represented by a formula (II); and (b) carrying out dechlorination reaction on the compound represented by the formula (II) under the action of a reducing agent to obtain a compound represented by a formula (III). According to the preparation method, starting raw materials, process routes and post-treatment processes are different, the raw materials are simple and easy to obtain, the cost is low, and the preparation method is suitable for laboratory small-scale preparation and industrial production.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a synthesis method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine. Background technique [0002] 4-Methyl-7H-pyrrolo[2,3-d]pyrimidine is an important pharmaceutical intermediate that can be used to synthesize TrK enzyme inhibitors, JAK enzyme inhibitors and E1 activating enzyme inhibitors (WO2011133637A2, WO2015083028, WO2007092213, etc.). However, for the preparation of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine, so far there are few domestic and foreign reports (WO2007092213). In view of this, the emergence of a new synthetic method is necessary. Invention content: [0003] The invention provides a synthetic method of 4-methyl-7H-pyrrolo[2,3-d]pyrimidine. The method is different in starting raw material, process route and post-treatment process. The raw material is simple and easy to obtain, and the cost is low. Inexpensive and easy to operate. [0004] In order to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 陆国彪金煜东戎祖磊孙飞强罗峰杜强强
Owner HANGZHOU ALLSINO CHEM
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