4,5,6-TRIFLUOROPYRIMIDINE Chemical Properties

Boiling point:

83-85°C

Density 

1.4609

refractive index 

1.4087

Flash point:

83-85°C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetone, Chloroform, Methanol (Slightly)

form 

Oil

pka

-6.10±0.26(Predicted)

color 

Clear Colourless to Light Yellow

CAS DataBase Reference

17573-78-3

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

4,5,6-TRIFLUOROPYRIMIDINE Usage And Synthesis

Uses

4,5,6-Trifluoropyrimidine is a starting material for the preparation of O-linked pyrimidinamine-based compounds as deoxycytidine kinase inhibitors. These inhibitors are useful for treatment of cancer.

Synthesis

The general procedure for the synthesis of 4,5,6-trifluoropyrimidine from 4,5,6-trichloropyrimidine was as follows: first, 7160 mL of cyclobutanesulfone and 3876 g of potassium fluoride (KF) were added to an autoclave and stirred for 1 hour at 150 °C. Subsequently, 700 mL of the cyclobutanesulfone was removed by reduced pressure distillation to dry the mixture. The mixture was cooled to 90 °C and the air in the kettle was replaced with nitrogen. Next, a solution of 3122 g of 4,5,6-trichloropyrimidine and 2386 g of dried cyclobutanesulfone preheated to 45 °C was added. The reaction vessel was sealed after the rapid addition of 10 g of CNC catalyst and 20.5 g of nitrobenzene. The mixture was heated to 200 °C and the reaction was stirred for 5 hours, then warmed to 220 °C to continue the reaction for 11 hours. The maximum total pressure was controlled at 6.5 bar during the reaction. Upon completion of the reaction, the mixture was cooled to 40 °C with stirring and the product was slowly depressurized and transferred to an ice-cold receiver. Subsequently, the internal temperature was slowly raised to 150 °C and the product was distilled first at atmospheric pressure and then at reduced pressure. Redistillation of the crude product gave 1540 g of 4,5,6-trifluoropyrimidine (66% of theoretical yield) as a colorless liquid.

References

[1] Patent: US2006/9643, 2006, A1. Location in patent: Page/Page column 5

4,5,6-TRIFLUOROPYRIMIDINE(17573-78-3)Related Product Information

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• 2-AMINO-4-TRIFLUOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER
• 2,4,6-TRIFLUOROPYRIMIDINE,2,4,6-Trifluoropyrimidine,98%,2,4,6-Trifluoropyrimidine 98%
• 5-CHLORO-2,4,6-TRIFLUOROPYRIMIDINE
• 4-AMINO-2,5,6-TRIFLUOROPYRIMIDINE
• 4,5,6-TRIFLUORO-2-TRIFLUOROMETHYL-PYRIMIDINE
• 2,4,5,6-Tetrafluoropyrimidine
• 4,5,6-TRIFLUOROPYRIMIDINE
• 4,6-DIFLUOROPYRIMIDINE