Ammonia → 5-Bromo-2-(trifluoromethyl)pyrimidine

A mixture of potassium fluoride (1.77 g) and cuprous iodide (5.79 g) was stirred and heated together using a heat gun under vacuum (˜1 mm) for 20 min. After cooling, dimethyl formamide (20 ml) and N-methyl pyrrolidinone (20 ml) were added followed by (trifluoromethyl)trimethylsilane (4.1 ml) and 5-bromo-2-iodopyrimidine (6.5 g). The mixture was stirred at rt for 5 h and then the brown solution was poured into 6N ammonia solution. The product was extracted into ethyl acetate and the extracts were washed with sodium bicarbonate solution and brine and then dried (Na2SO4) and evaporated. Chromatography on silica gel (elution with 20-50% dichloromethane in pentane) gave the title compound (D13) as a white solid (2.4 g). 1H NMR (CDCl3): 8.97 (2H, s).

1. temperatureheated together
2. customfor 20 min
3. temperatureAfter cooling
4. stirringThe mixture was stirred at rt for 5 h
5. extractionThe product was extracted into ethyl acetate
6. washthe extracts were washed with sodium bicarbonate solution and brine
7. dry with materialdried (Na2SO4)
8. customevaporated

ORD record

ord-ae5fe7320ba346d08180f24384b684e7

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07846922B2