Method for preparing 4-chloro-7H-pyrrolo[2,3-d] pyrimidine

A 3-d, pyrrole technology, applied in the field of chemical drug synthesis, can solve the problems of high toxicity of ammonia gas, difficult operation of ozone, unfavorable mass production and the like

Inactive Publication Date: 2019-10-18
NANJING GEAR PHARMA & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the final yield can reach 70%, the ammonia gas is more toxic in the reaction, and the redox reaction of ozone is not easy to operate, which is not conducive to industrial mass production

Method used

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  • Method for preparing 4-chloro-7H-pyrrolo[2,3-d] pyrimidine
  • Method for preparing 4-chloro-7H-pyrrolo[2,3-d] pyrimidine
  • Method for preparing 4-chloro-7H-pyrrolo[2,3-d] pyrimidine

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Embodiment Construction

[0017] In order to understand the present invention more clearly, we further illustrate in conjunction with reaction example:

[0018] 1, the synthesis of (II): under the protection of nitrogen, get 50g (I), 200ml ammoniacal liquor, 38gN-methyl-N-morpholine oxide, 200ml dichloromethane is added in the reaction bottle. And the reaction was placed in an oil bath with stirring and the temperature was raised to 35-40°C and stirred for 24h. TLC traced the reaction process, and when the raw material point disappeared or did not change, the reaction was stopped, and the solvent was removed to obtain 40.5 g of compound II, with a yield of 90%.

[0019] 2. Synthesis of (III): Under the protection of nitrogen, take 10g of (II), 2g of transition metal ruthenium, 38g of sodium periodate, and 50ml of anhydrous acetonitrile into the reaction flask, heat the oil bath to 60°C and stir for reaction. TLC detection, when the raw material point disappears or no longer changes, we carry out post-...

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Abstract

The invention provides a method for preparing 4-chloro-7H-pyrrolo[2,3-d] pyrimidine. The method comprises the following steps: (1) enabling a compound of a formula (I) shown in the specification to react with ammonium hydroxide in a dichloromethane solvent so as to be converted into a compound of a formula (II) shown in the specification; (2) enabling the compound of the formula (II) to react under catalysis of sodium periodate and a transition metal ruthenium so as to obtain a compound of formula (III) shown in the specification; and (3) under an acid condition, performing a ring-closure reaction on the compound of the formula (III) self so as to generate a target product, namely the 4-chloro-7H-pyrrolo[2,3-d] pyrimidine. Initial raw materials for preparing the 4-chloro-7H-pyrrolo[2,3-d]pyrimidine by using the method are easy to obtain, waste liquids are easy to treat in the reaction process, reaction conditions at different steps are gentle, purification is easy to implement, the operation is simple and feasible, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to a preparation method for 4-chloro-7H-pyrrolo[2,3-d]pyrimidine. Background technique [0002] Rheumatoid arthritis (RA) also affects approximately 1% of adults worldwide. [0003] JAK / STAT is an important cytokine signaling pathway, which is related to rheumatoid arthritis. In recent years, drugs for the treatment of rheumatoid arthritis (RA) have been developed rapidly. Pyrrolopyrimidine compounds have good physiological activity and pharmacological activity, and the intermediate 4-chloro-7H-pyrrolo[2,3-d]pyrimidine is a synthetic treatment of JAK inhibitor ruxolitinib for rheumatoid arthritis. , An important intermediate of Tofacitinib. Known related synthetic methods have problems such as high starting material prices and low yields. These problems need to be further optimized to meet market needs. With the successive listing of tofacitinib and ruxolitinib, d...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 叶家海穆灿灿
Owner NANJING GEAR PHARMA & TECH CO LTD
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