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Method for synthesizing 5-cyano pyridine nucleoside derivatives

A technology of cyanopyrimidine nucleoside derivatives and pyrimidine nucleosides, which is applied in the field of preparation of 5-cyanopyrimidine nucleoside derivatives, can solve the problems of difficult recovery of solvents, harsh reaction conditions, expensive raw materials, etc., and achieve easy recovery and The effect of repeated use and easy operation

Inactive Publication Date: 2012-06-27
HENAN NORMAL UNIV
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Problems solved by technology

[0004] The results of literature research show that although there are some relatively mature methods for the synthesis of 5-cyanopyrimidine nucleoside derivatives, these methods generally have harsh reaction conditions, expensive raw materials, rare materials, high toxicity of reagents, and difficult recovery of solvents. , great harm to the environment and other disadvantages

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  • Method for synthesizing 5-cyano pyridine nucleoside derivatives
  • Method for synthesizing 5-cyano pyridine nucleoside derivatives

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example 1

[0016] Synthesis of Example 1.5-cyano-2'-deoxy-3',5'-di-O-acetylated uridine

[0017] Acetic anhydride and 2'-deoxy-3',5'-di-O-acetyluridine-5-carbaldehyde oxime (355 mg, 1 mmol) were added to a 25 mL flask. Then, the reaction bottle was placed in an oil bath, and reacted at a temperature of 140° C. for 3 hours. After the reaction, concentrate under reduced pressure (recover acetic anhydride), add water, precipitate 5-cyano-2'-deoxy-3',5'-bis-O-acetylated uridine crude product, and filter with suction. The crude product was recrystallized from ethanol-water to obtain 296 mg (88%) of the product 5-cyano-2'-deoxy-3',5'-bis-O-acetylated uridine.

[0018] White solid.mp 161-162℃; 1 H NMR (DMSO-d 6 , 400MHz) δ: 2.04(s, 6H, 2CH 3 ), 2.36-2.39(m, 1H, CH), 2.51-2.55(m, 1H, CH), 4.22-4.25(m, 3H, CH, CH2), 5.18(s, 1H, CH), 6.06(t, J=6.4Hz, 1H, CH), 8.56(s, 1H, CH), 12.07(s, 1H, NH); 13 C NMR δ: 20.92, 21.10, 36.96, 63.81, 73.80, 82.32, 86.50, 89.15, 114.58, 149.35, 150.16, 160.37,...

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Abstract

The invention discloses a method for synthesizing 5-cyano pyridine nucleoside derivatives. Pyridine nucleoside-5-formaldehyde oxime is added into acetic anhydride to be heated and dehydrated to efficiently generate 5-cyano pyridine nucleoside. The reaction process is simple; needed raw materials are easy to obtain; reagents are safe; and the acetic anhydride not only can be as a dehydrating agent but also can be used as a reaction solvent, is easy to recycle and can be repeatedly utilized. The method for synthesizing the 5-cyano pyridine nucleoside derivatives has the advantages of simple and feasible reaction process, cleanness and high efficiency, thereby being applicable to industrial production in a large scale.

Description

technical field [0001] The invention relates to the fields of synthetic chemistry and medicine, and mainly relates to a preparation method of 5-cyanopyrimidine nucleoside derivatives. Background technique [0002] 5-cyanopyrimidine nucleoside is an unnatural 5-substituted pyrimidine nucleoside derivative. Such compounds not only have significant biological activity (such as antiviral activity, etc.), but also are good intermediates of many antiviral and antitumor drugs. In addition, 5-cyanopyrimidine nucleoside is also an important raw material for gene medicine and genetic engineering research. It has been widely used in the synthesis of DNA fragments to investigate the effect of pyrimidine nucleoside 5-substituents on the base interaction in DNA. . Therefore, with the continuous development of genetic engineering research and DNA synthesis technology, the demand for such compounds is constantly increasing. [0003] At present, the synthesis of 5-cyanopyrimidine nucleosi...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/08C07H1/00C07H19/073C07D239/557
Inventor 张新迎范学森蒋盼盼郭胜海
Owner HENAN NORMAL UNIV
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