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Preparation method of antitumor drug tegafur

A tegafur and anti-tumor technology, applied in the direction of organic chemistry, etc., can solve the problems of many impurities, harsh reaction conditions, cumbersome operation, etc., and achieve the effects of stable reaction process, easy purification, and simplified production operations

Active Publication Date: 2020-01-07
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the problems of harsh reaction conditions, cumbersome operation and many impurities in the current preparation process, the present invention provides a method suitable for industrial production of tegafur

Method used

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  • Preparation method of antitumor drug tegafur
  • Preparation method of antitumor drug tegafur
  • Preparation method of antitumor drug tegafur

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Add 5-fluorouracil (13.00g, 0.10mol), sodium acetate (16.40g, 0.20mol), and tetrabutylammonium iodide (1.48g, 4.00mmol) into 150mL of purified water, and stir until the solids are completely dissolved. A solution of 2-benzoyloxytetrahydrofuran (27.00 g, 0.14 mol) in dichloromethane (150 mL) was added. The reaction system was warmed up to 35°C for 3 h. After the reaction was completed, the reaction liquid was cooled to room temperature, and the dichloromethane layer was separated, washed with purified water (100 mL×3), washed with saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain tegafur with a yield of 95.20%, which was detected by HPLC, wherein t R =13.930min is tegafur, with a purity of 99.973% and a maximum of 0.011% impurity.

Embodiment 2

[0031]Add 5-fluorouracil (13.00g, 0.10mol), sodium acetate (8.20g, 0.10mol), tetrabutylammonium iodide (1.48g, 4.00mmol) into 150mL of purified water, and stir until the solids are completely dissolved. A solution of 2-benzoyloxytetrahydrofuran (27.00 g, 0.14 mol) in dichloromethane (150 mL) was added. The reaction system was warmed up to 30°C for 5 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the dichloromethane layer was separated, washed with purified water (100 mL×3), washed with saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain tegafur with a yield of 92.64%, which was detected by HPLC, wherein t R =13.807min is tegafur with a purity of 99.895% and a maximum of 0.018% impurity.

Embodiment 3

[0033] Add 5-fluorouracil (13.00g, 0.10mol), sodium acetate (6.56g, 0.08mol), tetrabutylammonium iodide (1.48g, 4.00mmol) into 150mL of purified water, and stir until the solids are completely dissolved. A solution of 2-benzoyloxytetrahydrofuran (27.00 g, 0.14 mol) in dichloromethane (150 mL) was added. The reaction system was warmed up to 35°C for 6 h. After the reaction was completed, the reaction solution was cooled to room temperature, and the dichloromethane layer was separated, washed with purified water (100 mL×3), washed with saturated brine (100 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to dryness under reduced pressure to obtain tegafur with a yield of 86.17%, which was detected by HPLC, wherein t R =13.904min is tegafur, with a purity of 99.729% and a maximum of 0.036% impurity.

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Abstract

The invention provides a preparation method of tegafur. The method mainly comprises the following steps: at room temperature, reacting 5-fluorouracil with 2-benzoyloxy tetrahydrofuran under the actionof an inorganic base and a phase transfer catalyst to obtain tegafur. Compared with the prior art, the method has the advantages of simple and easily available raw materials, simple operation, mild reaction conditions, stable quality, high yield, no pollution to the environment and suitability for industrial production, the purity of the obtained product is as high as 99.7%, and the maximum single impurity content is less than 0.1%.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of an antitumor drug tegafur. Background technique [0002] The compound involved in the present invention is Tegafur (also known as Tegafur, Ftorafur, FT207), chemical name: 1-(tetrahydro-2-furyl)-5-fluoro-2,4(1H,3H)-pyrimidinedione , is one of the pyrimidine anticancer drugs, it is the prodrug of 5-fluorouracil, it has inhibitory effect on most solid tumors, the structural formula is as follows: [0003] [0004] Tegafur is a derivative of 5-fluorouracil, which was first synthesized by Hiller of the former Soviet Union in 1967 and listed in Japan in 1974. It was successfully developed by Shandong Jinan Pharmaceutical Factory in 1979 in my country. The anti-cancer spectrum and curative effect of tegafur are similar to 5-fluorouracil. 450 Under the catalysis of activating enzyme, it is converted into 5-fluorouracil, and then about...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04
CPCC07D405/04Y02P20/584
Inventor 吴素珍王秀娟
Owner LUNAN PHARMA GROUP CORPORATION
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