Method for preparing high purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine

A 3-d, high-purity technology, used in the fields of medicine and chemical industry, can solve the problems of difficult to obtain high-purity products, and achieve the effect of shortening the production process and mild conditions

Inactive Publication Date: 2014-10-29
苏州科捷生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

According to the existing preparation methods, it is difficult to obtain high-purity products

Method used

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  • Method for preparing high purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Example 1: Synthesis of 5-bromo-4-chloro-7H-pyrrole [2,3-d] pyrimidine (compound 2)

[0012] 4-Chloro-7H-pyrrole[2,3-d]pyrimidine (10g, 0.06mol) was dissolved in DMF (130ml), and a solution of NBS (11.6g, 0.06mol) in DMF (70ml) was added dropwise at 0°C, Finished in about half an hour. Stir at room temperature for 1 hour, then add methanol (165 mL) and stir for 1 hour. Distilled under reduced pressure, the residue was washed with methanol, and vacuum-dried to obtain 13.2 g of white solid (2), yield: 97.8%.

Embodiment 2

[0013] Example 2: Synthesis of 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine (compound 3)

[0014] Compound 2 (5 g, 0.02 mol) was dissolved in tetrahydrofuran (100 ml), and 2.5M n-butyllithium (25.8 ml, 0.06 mol) was added dropwise at -78°C for about half an hour. After continuing to stir for half an hour, methyl iodide (4 ml, 0.06 mol) was added dropwise for about half an hour, and then naturally warmed to room temperature, and the reaction was rapidly quenched with 20 ml of saturated aqueous ammonium chloride. Extract with ethyl acetate, combine the organic phases, dry and concentrate. The crude product was recrystallized from DMF-methanol to obtain 2.3 g of white crystals (3), yield: 64.4%, HPLC purity: 99.8%.

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Abstract

The invention discloses a method for preparing high purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine. A starting material 4-chloro-7H-pyrrole [2,3-d] pyrimidine is subjected to a bromination reaction and methylation; a crude product is recrystallized to obtain high purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine. The method has mild and simple reaction conditions, low cost, high yield and simple operation, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing high-purity 4-chloro-5-methyl-7H-pyrrole[2,3-d]pyrimidine, which belongs to the technical fields of medicine and chemical industry. Background technique [0002] 4-Chloro-5-methyl-7H-pyrrole[2,3-d]pyrimidine and its derivatives are widely used in the field of medicine, and have good antidepressant, antitumor, antibacterial and other biological activities. According to the existing preparation method, it is difficult to obtain a high-purity product. Contents of the invention [0003] The purpose of the present invention is to optimize the synthesis method to prepare high-purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine, the method raw materials are easy to get, cheap, high yield, mild reaction conditions, suitable for in industrial production. [0004] The reaction scheme is as follows: [0005] [0006] A method for preparing high-purity 4-chloro-5-methyl-7H-pyrrole [2,3-d] pyrimidine descri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 黄传满邵东
Owner 苏州科捷生物医药有限公司
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