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Synthesis method of 5-(trifluoromethyl) uracil

A technology of trifluoromethyluracil and uracil, which is applied in the field of preparation of 5-trimethyluracil, can solve the problems of high price, inconvenient purification, unsuitable for industrial operation, etc.

Inactive Publication Date: 2014-06-25
NANJING ANYUAN BIO PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the above synthesis method, bromotrifluoromethane and iodotrifluoromethane are gases at normal temperature, which are not suitable for industrial operation, relatively expensive, and inconvenient for purification.

Method used

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  • Synthesis method of 5-(trifluoromethyl) uracil
  • Synthesis method of 5-(trifluoromethyl) uracil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] 1) Add 100 g (0.89 mol) of raw material uracil, 460.7 g (2.95 mol) of sodium trifluoromethanesulfinate and 5.0 L of water into the reaction flask, and cool in an ice bath.

[0012] 2) Slowly add 474 g (5.27 moles) of tert-butyl hydroperoxide dropwise, keeping the system temperature below 10°C. After the dropwise addition, the temperature was naturally raised to room temperature, 20 g of copper sulfate was added, and stirring was continued at 250 rpm.

[0013] 3) LCMS detects that the raw material reacts almost completely after 5 days

[0014] 4) Add saturated aqueous sodium thiosulfate solution to quench the peroxide, stir for 1 hour and then filter.

[0015] 5) The filtrate was extracted three times with 5.5 L of ethyl acetate, the organic phases were combined, washed with water (3 L) and saturated brine (3 L), dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain a white solid.

[0016] 6) The white solid obtained in 5 was beaten with 550 mL (EtOAc...

Embodiment 2

[0018] 1) Add 100 g (0.89 mol) of raw material uracil, 460.7 g (2.95 mol) of sodium trifluoromethanesulfinate and 5.0 L of water into the reaction flask, and cool in an ice bath.

[0019] 2) Slowly add 474 g (5.27 moles) of tert-butyl hydroperoxide dropwise, keeping the system temperature below 10°C. After the dropwise addition, the temperature was naturally raised to room temperature, 20 g of copper sulfate was added, and stirring was continued at 500 rpm.

[0020] 3) LCMS detects that the raw material reacts almost completely after 5 days

[0021] 4) Add saturated aqueous sodium thiosulfate solution to quench the peroxide, stir for 1 hour and then filter.

[0022] 5) The filtrate was extracted three times with 5.5 L of ethyl acetate, the organic phases were combined, washed with water (3 L) and saturated brine (3 L), dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain a white solid.

[0023] 6) The white solid obtained in 5 was beaten with 550 mL (EtOAc...

Embodiment 3

[0025] 1) Add 100 g (0.89 mol) of raw material uracil, 460.7 g (2.95 mol) of sodium trifluoromethanesulfinate and 5.0 L of water into the reaction flask, and cool in an ice bath.

[0026] 2) Slowly add 474 g (5.27 moles) of tert-butyl hydroperoxide dropwise, keeping the system temperature below 10°C. After the dropwise addition, the temperature was naturally raised to room temperature, and continued to stir at 250 per minute for 5 days.

[0027] 3) Add saturated aqueous sodium thiosulfate solution to quench the peroxide, stir for 1 hour and then filter.

[0028] 4) The filtrate was extracted three times with 5.5 L of ethyl acetate, the organic phases were combined, washed with water (3 L) and saturated brine (3 L), dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain a white solid.

[0029] 5) The white solid obtained in 4 was beaten with 550 mL (EtOAc:PE=1:10) for 2 hours, filtered, the filter cake was washed with PE, and dried to obtain 75 g of the produc...

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Abstract

The invention discloses a synthesis method of 5-(trifluoromethyl) uracil. The method comprises the step of fluorinating uracil by use of sodium trifluoromethanesulfinate and tert-butyl hydrogen peroxide in the presence of an effective dose of catalyst, wherein the catalyst is copper sulfate and the weight of the catalyst accounts for 10-50% of that of the uracil; furthermore, by regulating the equivalent number of the sodium trifluoromethanesulfinate, the cost consumed by raw materials can be minimized, and the equivalent number is 1.5.

Description

technical field [0001] The invention relates to the field of fluorine chemical industry, in particular to a preparation method of 5-trimethyluracil. Background technique [0002] Trifluoromethyluracil is a very useful uracil derivative and also a very important intermediate compound, especially for the field of pharmacy. There are relatively few reports on the synthesis method of trifluoromethyluracil, and the general method is to synthesize uracil with bromotrifluoromethane or iodotrifluoromethane. The route is as follows: [0003] [0004] However, in the above synthesis method, bromotrifluoromethane and iodotrifluoromethane are gases at normal temperature, which are not suitable for industrial operation, relatively expensive, and inconvenient to purify. Contents of the invention [0005] The object of the present invention is to provide a process for the preparation of 5-trifluoromethyluracil starting from readily available reagents. A process has now been found f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCC07D239/54
Inventor 王小龙熊涛
Owner NANJING ANYUAN BIO PHARMA TECH CO LTD
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