Triethylamine → Pyrimidine, 5-(bromomethyl)-2-[4-(trifluoromethoxy)phenyl]-

Participants

Reaction Conditions

Reaction Steps

Mesyl chloride (0.55 mL, 7.0 mmol) was added to a solution of alcohol 91 (0.951 g, 3.52 mmol) and Et3N (1.5 mL, 10.8 mmol) in THF (40 mL) at 0° C. and the mixture was stirred at 0° C. for 1 h. The mixture was partitioned between EtOAc and water, and the organic layer was dried and evaporated to give an oil, which was dissolved in acetone (100 mL). LiBr (6.10 g, 70.2 mmol) was added and the mixture was refluxed under N2 for 1 h, then filtered and evaporated. The residue was partitioned between EtOAc and water, and the organic layer was dried and evaporated. Column chromatography on silica gel (eluting with CH2Cl2) gave 5-(bromomethyl)-2-[4-(trifluoromethoxy)phenyl]pyrimidine (92) (1.097 g, 94%) as a white solid: mp 80-81° C.; 1H NMR (CDCl3) δ 8.82 (s, 2H), 8.50 (d, J=9.0 Hz, 2H), 7.32 (d, J=9.0 Hz, 2H), 4.48 (s, 2H). APCI MS m/z 333, 335 [M+H]+.

Provenance & Evidence