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Preparation method of 4,5,6-trifluoro-pyrimidine compound

A technology of trifluoropyrimidine and compounds, applied in the direction of organic chemistry, can solve the problems of harsh process conditions, unstable catalysts, high reaction temperature, etc., and achieve the effects of high yield and purity, low production cost and low reaction temperature

Active Publication Date: 2015-01-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction still needs to be carried out under high pressure, the reaction temperature is relatively high, and the catalyst reported is specially made. The catalyst is extremely unstable in the air and needs to be stored in an inert gas, and the process conditions are relatively harsh.

Method used

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  • Preparation method of 4,5,6-trifluoro-pyrimidine compound
  • Preparation method of 4,5,6-trifluoro-pyrimidine compound
  • Preparation method of 4,5,6-trifluoro-pyrimidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 58 g (1.00 mol) of potassium fluoride and 300 mL of N,N-dimethylformamide (DMF) into a 500 ml four-necked flask equipped with mechanical stirring, a thermometer, and a vacuum distillation device, and heat up to about 50 °C , adjust the vacuum degree to -0.090MPa, a small amount of DMF can be distilled during this period, continue to heat up to about 70-80 ℃, distill about 80-100 mL of DMF to remove the moisture in the raw materials and solvent as much as possible, then remove the vacuum, and cool down to 60 -65°C, add 3.2 g (0.01 mol) tetrabutylammonium bromide and 32.2 g (0.19 mol) 4,6-dichloro-5-fluoropyrimidine, and stir the reaction at this temperature for 5 h. After the complete reaction of the raw materials was detected by gas chromatography, the reaction device was changed to an atmospheric distillation device, and the fraction with a gas phase temperature of 85-86°C was collected to obtain 21.5 g of colorless and transparent liquid 4,5,6-trifluoropyrimidine, ...

Embodiment 2

[0026] Add 58 g (1.00 mol) of potassium fluoride and 300 mL of dimethyl sulfoxide (DMSO) into a 500 ml four-necked flask equipped with mechanical stirring, a thermometer, and a vacuum distillation device, raise the temperature to about 90 °C, and adjust the vacuum degree To -0.095MPa, a small amount of DMSO can be distilled during this period, continue to heat up to about 100-110 ℃, distill about 80-100 mL DMSO to remove the moisture in the raw material and solvent as much as possible, then remove the vacuum, cool down to 55-60 ℃, Add 1.6 g (0.005 mol) tetrabutylammonium bromide and 32.2 g (0.19 mol) 4,6-dichloro-5-fluoropyrimidine, and stir the reaction at this temperature for 7 h. After the reaction of the raw materials was detected by gas chromatography, the reaction device was changed to an atmospheric distillation device, and the fraction with a gas phase temperature of 85-86 ° C was collected to obtain 21.9 g of 4,5,6-trifluoropyrimidine, a colorless transparent liquid, w...

Embodiment 3

[0028] Add 174g (3.00 mol) of potassium fluoride and 600 mL of sulfolane into a 1000 ml four-necked flask equipped with mechanical stirring, a thermometer, and a vacuum distillation device, raise the temperature to about 130°C, and adjust the vacuum to -0.098MPa. Produce a small amount of sulfolane, continue to heat up to about 140-150 °C, distill about 80-100 mL of sulfolane to remove the moisture in the raw material and solvent as much as possible, then remove the vacuum, cool down to 60-65 °C, add 3.2 g (0.01 mol) tetra Butylammonium bromide and 64.5g (0.39mol) 4,6-dichloro-5-fluoropyrimidine were stirred at this temperature for 5h. After the complete reaction of the raw materials was detected by gas chromatography, the reaction device was changed to an atmospheric distillation device, and the fraction with a gas phase temperature of 85-86 ° C was collected to obtain 47.5 g of colorless and transparent liquid 4,5,6-trifluoropyrimidine, which was detected by GC with a purity ...

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Abstract

The invention discloses a preparation method of a 4,5,6-trifluoro-pyrimidine compound, which is prepared by taking 4,6-dichloro-5-fluorine pyrimidine as a raw material and reacting at ordinary pressure in the presence of a fluorinated reagent, a phase-transfer catalyst and a high-polarity aprotic solvent. The preparation method disclosed by the invention has the advantages of simple reaction process condition, low reaction temperature and short reaction time and is low in production cost, and free of high-pressure equipment due to reaction under ordinary pressure; and the obtained product achieves higher yield and purity more than 80% and 97% respectively.

Description

technical field [0001] The invention relates to a preparation method of 4,5,6-trifluoropyrimidine compound. Background technique [0002] 4,5,6-Trifluoropyrimidine is an important intermediate for the synthesis of new fungicides. It is of great practical significance to study its synthesis and develop a process route suitable for industrial production. [0003] Halogenated pyrimidines and their application as a method for reducing parasites studied by U. Heinemann, H. Gaya, and P. Gerders of Bayer Company in Germany (CN1146550C), with 4,5,6-trichloropyrimidine To prepare 4,5,6-trifluoropyrimidine as starting material, the method needs to be carried out in two steps and high pressure conditions are used. [0004] Preschek and Majorhold in Germany reported the method of using 4,5,6-trichloropyrimidine as a raw material to directly prepare 4,5,6-trifluoropyrimidine through one-step reaction (CN1718572A). However, the reaction still needs to be carried out under high pressure,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/30
Inventor 丁成荣张国富许莉沈方烈
Owner ZHEJIANG UNIV OF TECH
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