Sodium hydride → HCID 23086841, compound

Temperature

10 °C

Dissolved in 70 ml DMF, 40.8 g 4-fluoro-3-(trifluoromethyl)-phenol are stirred under an inert gas atmosphere and cooled to 10° C. To this, 5.8 g sodium hydride are added slowly under vigorous stirring. The mixture is then allowed to warm up to room temperature and stirred for 1 h. Then, a solution of 19.9 g 4,6-Dichloro-5-aminopyrimidine in 50 ml DMF is added dropwise and the reaction mixture is heated for 24 h at 80° C. After quenching with water and concentration under reduced pressure the crude mixture is extracted twice with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride and finally dried over magnesium sulfate and charcoal. The dark brown oily residue is dissolved in 100 ml diethylether and treated with 100 ml hexane. The resulting title compound crystallizes as a colorless solid with a melting point of 104-105° C.

1. temperatureto warm up to room temperature
2. temperaturethe reaction mixture is heated for 24 h at 80° C
3. customAfter quenching with water and concentration under reduced pressure the crude mixture
4. extractionis extracted twice with ethyl acetate
5. washThe combined organic phases are washed with water and saturated sodium chloride
6. dry with materialfinally dried over magnesium sulfate and charcoal
7. dissolutionThe dark brown oily residue is dissolved in 100 ml diethylether
8. additiontreated with 100 ml hexane
9. customThe resulting title compound crystallizes as a colorless solid with a melting point of 104-105° C.

ORD record

ord-33a82fc94490482788953be2959fe0dc

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367682B2