Synthesis method of 4-chloropyrrolopyrimidine compound

A technology of chloropyrrolopyrimidine and a synthesis method, which is applied in the field of synthesis of 4-chloropyrrolopyrimidine compounds, can solve the problems of long synthesis route, high toxicity of raw materials, environmental pollution and the like, and achieves short synthesis route, low toxicity of raw materials and pollution. light effect

Inactive Publication Date: 2020-07-28
南京普锐达医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art of using 4-chloropyrrolopyrimidine as a reaction substrate to generate 4-amino-5-iodo-7methylpyrrolopyrimidine, there are long synthetic routes, low yield, high toxicity of raw materials, and the shortcomings of environmental pollution

Method used

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  • Synthesis method of 4-chloropyrrolopyrimidine compound
  • Synthesis method of 4-chloropyrrolopyrimidine compound
  • Synthesis method of 4-chloropyrrolopyrimidine compound

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preparation example Construction

[0019] A kind of synthetic method of 4-chloropyrrolopyrimidine compound, it is characterized in that: comprise the following steps:

[0020] Step 1: Mix 4-hydroxypyrrolopyrimidine, phosphorus oxychloride and organic base in a weight ratio of 1:5-10:3-7 and carry out chlorination reaction in a certain temperature range for 2-5 hours, and depressurize the mixture after cooling Concentrate to remove excess phosphorus oxychloride, add water to quench, and then extract with an organic solvent, dry, and concentrate to obtain the product 4-chloropyrrolopyrimidine.

[0021] Step 2: Dissolve 4-chloropyrrolopyrimidine in ethanol, start to add the ethanol solution of ammonia dropwise, after adding ethanol, control the reaction at 60°C for 2-3 hours, and remove excess ethanol after the reaction to obtain 4-aminopyrrolopyrimidine pyrimidine.

[0022] Step 3: Dissolve 4-aminopyrrolopyrimidine in dichloromethane, add iodosuccinimide in batches at room temperature, and stir and react at room...

specific Embodiment

[0030] (1) After mixing 100g of 4-hydroxypyrrolopyrimidine, 400g of phosphorus oxychloride and 500g of triethylamine and diisopropylethylamine, the temperature is controlled at 50°C, and the chlorination reaction is carried out for 3 hours, and the mixture is cooled Concentrate under reduced pressure to remove excess phosphorus oxychloride, add water to quench, then extract with organic solvent, dry, and concentrate to obtain the product 4-chloropyrrolopyrimidine.

[0031] (2) Dissolve the generated 4-chloropyrrolopyrimidine in 500g of ethanol, start to add the ethanol solution of ammonia dropwise, and keep the reaction at 60°C for 2 hours. The excess ethanol was evaporated to obtain 4-aminopyrrolopyrimidine.

[0032] (3) Dissolving 4-aminopyrrolopyrimidine in 200 g of dichloromethane liquid, adding iodosuccinimide in batches at room temperature, and stirring and reacting at room temperature for 13 hours, after the reaction was completed, the solid insolubles were removed by f...

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Abstract

The invention particularly relates to a synthetic method of a 4-chloropyrrolopyrimidine compound. The method comprises the following steps: step 1, mixing 4-hydroxypyrrolopyrimidine, phosphorus oxychloride and an organic alkali according to a weight ratio of 1: (5-10): (3-7), carrying out a chlorination reaction in a certain temperature range, carrying out reduced pressure concentration to removeredundant phosphorus oxychloride, quenching, extracting, drying, and concentrating to obtain 4-chloropyrrolopyrimidine; step 2, dissolving 4-chloropyrrolopyrimidine in ethanol, starting to dropwise add an ethanol solution of ammonia, carrying out a reaction at a constant temperature, and removing excess ethanol to obtain 4-aminopyrrolopyrimidine; step 3, dissolving 4-aminopyrrolopyrimidine in dichloromethane, adding iodo-succinimide in batches at the room temperature, filtering to remove solid insoluble substances, and completely evaporating the filtrate to obtain 4-amino-5-iodopyrrolopyrimidine; and step 4, dissolving 4-amino-5-iodopyrrolopyrimidine in DMF, adding cesium carbonate and methyl iodide, carrying out a reflux reaction for 12 h, cooling, filtering, and evaporating to obtain theproduct namely 4-amino-5-iodine-7-methylpyrrolopyrimidine.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of a 4-chloropyrrolopyrimidine compound. Background technique [0002] In recent years, heterocyclic compounds have attracted extensive attention due to their wide application in medicinal chemistry research. Heterocyclic compounds are cyclic compounds containing at least two different elements as ring member atoms, the most common atoms including nitrogen, oxygen and sulfur. Heterocyclic compounds exist in abundance in nature, and are of great significance in our lives because they exist in various natural molecules such as hormones, antibiotics, and caffeine. Pyrimidine rings are heterocyclic aromatic compounds that widely exist in nature. Pyrimidines were recognized as an important building block of nucleic acids in the early days and are currently used in AIDS chemotherapy. [0003] 4-Chloropyrrolopyrimidine,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 王小波
Owner 南京普锐达医药科技有限公司
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