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5-fluorouracil drug intermediate, preparation method and application thereof

A technology of fluorouracil and reaction, which is applied in the field of synthesis of 5-fluorouracil drug intermediates, can solve the problems of high toxicity and side effects, difficulty in oral absorption, low fat solubility, etc., and achieve the effect of high reaction yield

Inactive Publication Date: 2011-11-02
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, its main disadvantages are low fat solubility, difficulty in oral absorption, and relatively large toxic and side effects.

Method used

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  • 5-fluorouracil drug intermediate, preparation method and application thereof
  • 5-fluorouracil drug intermediate, preparation method and application thereof
  • 5-fluorouracil drug intermediate, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Take 1.302g of 5-fluorouracil in a 100mL three-necked flask, add 20mL of water and 5mL of 37% formaldehyde, react at 55°C, track and detect with TLC, the reaction is complete in 6 hours, distill off the water, add 30mL of acetone, 0.174g of manganese dioxide is oxidized , TLC tracking, after 4 hours of reaction, filtered, and the filtrate was evaporated to dryness to obtain 1.29 g of 5-fluorouracil-1-carbaldehyde, with a yield of 81.6%.

[0037] Spectral data of 5-fluorouracil-1-carbaldehyde: 1 H NMR (500MHz, DMSO-d 6 , TMS) δ11.20 (s, 1H, NH of 5-FU), 8.20 (s, 1H, -CHO), 7.67 (d, 1H, FC=CH, 3 J FH =6.5Hz) 13 C NMR (125MHz, DMSO-d 6 , TMS) δ, 52.0, 49.5, 36.3; IR (KBr, cm -1 )v: 3116, 1722, 1652, 1558, 1450, 1396, 1378, 1243, 1181, 679; ESI-MS m / z: 157 [M-1] - .

[0038] The NMR was completed on the AVANCE-500 NMR analyzer of Bruker, Switzerland, the mass spectrometry was completed on the DECAX-30000 LCQ DecaXP Plus of Finnigan Mass Spectrometry Company of the Un...

Embodiment 2

[0040] Take 1.307g of 5-fluorouracil in a 100mL three-necked flask, add 2mL of formic acid and 1.12g of zinc oxide, 30mL of toluene, react at 110°C, TLC tracking detection, 20h complete reaction, cool to room temperature, filter to obtain solid and filtrate, and evaporate the filtrate to dryness , to obtain part of 5-fluorouracil-1-carbaldehyde; the filtered solid was dissolved in 20mL DMF, filtered, and the filtrate was evaporated to dryness to obtain 5-fluorouracil-1-carbaldehyde, the total of the two was 0.95g, and the yield was 60.3%.

Embodiment 3

[0042]Take 1.303g of 5-fluorouracil in a 100mL three-necked flask, add 3mL of formic acid, 1.5g of silica gel powder, and 30mL of toluene, and react at 110°C. TLC tracking detection, the reaction is complete after 20 hours, cooled to room temperature, filtered to remove the silica gel, and evaporated to dryness. 0.26 g of solid 5-fluorouracil-1-carbaldehyde was obtained with a yield of 16.45%.

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Abstract

The invention discloses a 5-fluorouracil drug intermediate, namely, 5-fluorouracil-1-methanal and discloses a preparation method thereof. The preparation method is characterized in that a low-toxic organic solvent is used as the solvent, and reaction can be completed in a shorter time and has higher reaction yield. The conversion rate of the raw material furthest reaches more than 90%; the yield of the product can furthest reach 80%; and the product is easily purified. The 5-fluorouracil-1-methanal provided by the invention can be used for synthesizing Schiff base compounds containing the 5-fluorouracil and prodrug carmofur containing the 5-fluorouracil.

Description

(1) Technical field [0001] The invention relates to a new method for synthesizing 5-fluorouracil drug intermediates. (2) Background technology [0002] According to the report of the World Health Organization, there are 20 million cancer patients in the world's total population of 6 billion, the incidence rate is about 3.3‰, and the average annual death rate of cancer patients is 12%. Statistics from the Ministry of Health of my country also show that there are currently 4.5 million cancer patients in my country, with an increase of about 2 million people every year. The national incidence rate of tumor is about 1.64‰. About 1.3 million people die from cancer every year in my country, and the mortality rate is 23%, which is higher than the global average annual mortality rate of 12%. In addition, according to a recent public statistics report by China Tumor Network, in less than 20 years, the incidence of cancer in my country has increased by 69%, and the death rate has in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/553
Inventor 熊静周书光黄祖胜晁国库王璐徐静
Owner WENZHOU UNIVERSITY
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