Bromine → 5-Bromo-6-(trifluoromethyl)pyrimidin-4-ol

Temperature

80 °C

Bromine (4.62 g) was added in one portion to a stirred solution of 4-trifluoromethylpyrimidin-6-one (4.3 g) and sodium acetate (10.53 g) in acetic acid (43 ml). After stirring for 2 hours, the reaction mixture was left to stand for a period of 3 days, after which time it was heated to 80° C. for 1 hour. After cooling to the ambient temperature (ca 22° C.), the solvent was evaporated under reduced pressure. The resultant orange solid was dissolved in ethyl acetate, and washed several times with water. The combined agueous washings were extracted with ethylacetate, and the combined organic layers were washed with aqueous sodium thiosulphate solution, followed by aqueous sodium bicarbonate solution and brine. After drying over magnesium sulphate, evaporation of the solvent under reduced pressure gave 5-bromo-4-trifluoromethylpyrimidin-6-one as white solid (4.8 g, mpt 226-227° C.); H NMR (CDC13), 8.05(s); 19 NMR (CDC13), -67.4(s). Preparation 4

1. waitthe reaction mixture was left
2. waitto stand for a period of 3 days
3. temperatureAfter cooling to the ambient temperature (ca 22° C.)
4. customthe solvent was evaporated under reduced pressure
5. dissolutionThe resultant orange solid was dissolved in ethyl acetate
6. washwashed several times with water
7. extractionThe combined agueous washings were extracted with ethylacetate
8. washthe combined organic layers were washed with aqueous sodium thiosulphate solution
9. dry with materialAfter drying over magnesium sulphate, evaporation of the solvent under reduced pressure

ORD record

ord-be30c429085a4c2b83a8fd8787ccd10a

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04990512