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Novel method for synthesizing uridine

A technology of uridine nucleoside and uracil, which is applied in the field of uridine nucleoside preparation, can solve the problem of low product purity, and achieve the effects of high purity, simple post-processing, and high conversion rate

Active Publication Date: 2011-03-30
ZHEJIANG XIANFENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method product purity is not high, is not suitable for industrialized large-scale production

Method used

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  • Novel method for synthesizing uridine
  • Novel method for synthesizing uridine

Examples

Experimental program
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Effect test

Embodiment 1

[0032] In a dry 1000ml four-neck flask, add a reflux tube, put 74.5g of D-ribose, 56g of uracil, and 7.45g of phosphotungstic acid, dissolve in 223.5g of dichloroethane, stir and heat up, stir and clarify at 75-80°C and then keep warm React for 3 hours, distill the reaction solution to 1 / 3 of the original volume under normal pressure, then distill under reduced pressure until no liquid comes out, add 300g of ethanol, stir and heat to reflux for 2 hours, cool to below 0-5°C, stir and crystallize for 1 hour, Suction filtration and drying to obtain 95.6 g of uridine as a white crystal powder. Yield 78.9%, HPLC 99.40%.

Embodiment 2

[0034] Take 74.5g of D-ribose, 56g of uracil, and 3.5g of phosphotungstic acid, dissolve them in 230g of dichloromethane, stir at 20-22°C for clarification, keep warm for 25 hours, then distill at atmospheric pressure to 1 / 3 of the original volume, and then depressurize Distilled until no liquid came out, added 592g of methanol, stirred and heated to reflux for 2 hours, cooled to below 0-5°C, crystallized for 6 hours, filtered with suction, and dried to obtain 102.6g of uridine as a white crystal powder with a yield of 84.7%. HPLC 99.57%.

Embodiment 3

[0036] Take 74.5g of D-ribose, 56g of uracil, and 3g of phosphotungstic acid, dissolve them in 447g of dichloromethane, stir and heat up to 35-40°C, stir and dissolve, then keep warm for 12 hours, and then distill at normal pressure to 1 / 4 of the original volume. Distill under reduced pressure until no liquid comes out, add 300g of ethanol, stir and heat under reflux for 1h, cool to below 0-5°C, crystallize for 3 hours, filter with suction, and dry to obtain 110.7g of uridine as a white crystal powder. The yield is 91.34%, HPLC 99.54%.

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Abstract

The invention discloses a method for synthesizing uridine. The method comprises the following steps of: adding uracil, D-ribose and a catalyst into a condensing agent, stirring and heating the mixed solution for reaction until the reaction temperature is between 20 and 80 DEG C, clarifying the mixed solution, keeping the temperature of the mixed solution for reaction for 3 to 25 hours, distilling the mixed solution at the normal pressure until the volume of the mixed solution is reduced to one fourth to one third of the original volume, after reaction, distilling the mixed solution under a reduced pressure until no liquid comes out, adding an organic solvent of which the mass is 3 to 8 times that of the D-ribose into the obtained product, stirring the mixed solution for dissolution,refluxing the mixed solution for 1 to 2 hours while stirring, cooling the mixed solution to the temperature of between 0 and 5 DEG C, crystallizing the mixed solution for 1 to 6 hours, filtering the mixed solution, and drying the filter cakes to obtain the uridine. The yield of the uridine is over 78 percent, and the HPLC of the uridine is over 99.35 percent. The method has the advantages of simple and reasonable process, good stability, safe production process, convenient operation and the suitability for industrialization.

Description

technical field [0001] The invention relates to a preparation method of uridine nucleoside. Background technique [0002] Uridine is an important intermediate of nucleoside and deoxynucleoside drugs. Nucleosides and deoxynucleosides are composed of nucleoside bases and ribose or deoxyribose in the form of glycosidic bonds. They are the basic substances that make up ribonucleic acid (RNA) and deoxyribonucleic acid (DNA), and are the basis of genetics . Nucleoside and deoxynucleoside series derivatives have a variety of biologically active substances, which can be used as medicines directly or indirectly, and play an important role in the treatment of many major diseases. [0003] At present, with the expansion of the scope of application of uridine triphosphate, diuridine tetraphosphate and uridine phosphatase inhibitors in the field of medicine and the application of uridine diphosphate glucose pyrophosphorylase gene , domestic and foreign scientific research institutions...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/067C07H1/00
Inventor 李凤军熊云茂
Owner ZHEJIANG XIANFENG TECH
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