Intermediate for synthesizing 2-chloroadenosine, synthesis process of intermediate and synthesis process of 2-chloroadenosine

Abstract

The invention relates to the technical field of organic synthesis, in particular to an intermediate for synthesizing 2-chloroadenosine, a synthesis process of the intermediate and a synthesis processof the 2-chloroadenosine. The synthesis process of the intermediate for synthesizing the 2-chloroadenosine comprises the following step: carrying out condensation reaction on 2,6-dichloropurine and tetraacetylribose under the catalytic action of 4-dimethylaminopyridine to form 2,3,5-4-triacetyl-2,6-dichloropurine riboside. The synthesis process is simple to operate, low in catalyst dosage, low incost, low in pollution and easy to industrially implement, and the yield and purity of the synthesized 2-chloroadenosine are higher.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an intermediate for synthesizing 2-chloroadenosine, its synthesis process and the synthesis process of 2-chloroadenosine. Background technique [0002] 2-Chloroadenosine, 2-chloro-6-aminopurine nucleoside, is an adenosine receptor agonist, which can effectively inhibit the expression of tumor metastasis-related genes mtal and mRNA, and then has inhibitory effects on various cancer cells , therefore, it is one of the newly developed anticancer agents in recent years. At the same time, it is also a drug intermediate of traditional Chinese medicine, and 2-chloroadenosine can be used to synthesize cladribine, an anti-leukemia drug. Therefore, the synthesis of 2-chloroadenosine is of great significance. [0003] In the prior art, there are many ways to synthesize 2-chloroadenosine, but there are many problems in the existing synthetic methods: for example, the catalyst use...

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Problems solved by technology

[0003] In the prior art, there are many ways to synthesize 2-chloroadenosine, but there are many problems in the existing synthetic methods: for example, the catalyst used is a heavy metal catalyst, the amount of catalyst used is large, the reaction conditions are harsh, the cost is high, the pollution is large, and the synthesis 2-Chloroadenosine was obtained in low yield and purity

For example, the use of tetraacetyl ribose, 2-chloroadenine and the catalyst - tin tetrachloride to form 2', 3', 5', triacetyl nucleosides, and then react with ammonia-methanol to form 2-chloroadenosine , the yield of this synthetic method is only about 62%, and tin tetrachloride is used as a catalyst, the pollution is large, and the cost is high. Simultaneously, 2-chloroadenine is not easy to purchase, and the cost is also high

For example, tetraacetyl ribose and 2,6-dichloropurine react under the catalysis of trifluoromethanesulfonic acid to form 2',3',5'-tri-O-acetyl-2,6-dichloropurine nucleoside , and then react with ammonia-methanol to form 2-chloroadenosine. This reaction uses trifluoromethanesulfonic acid as a catalyst, which is expensive and increases the production cost of 2-chloroadenosine. At the same time, the large amount of catalyst used makes the cost difficult Control is not conducive to industrialized production, and the purity and yield of 2-chloroadenosine formed by this process are also low

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