Bromine → 5-Bromo-4-(1-isopropyl-2-methylimidazol-5-yl)-2-(4-mesylanilino)pyrimidine

Participants

Reaction Conditions

Reaction Steps

Bromine (50 μl, 0.94 mmol) was added to a solution of 4-(1-isopropyl-2-methylimidazol-5-yl)-2-(4-mesylanilino)pyrimidine (Example 69; 350 mg, 0.94 mmol) in glacial acetic acid (3.5 ml). The mixture was heated at 60° C. for 140 minutes and the volatiles were then removed by evaporation. The residue was azeotroped with water to give a gum, which was then triturated with EtOAc to give a solid (470 mg). This crude product was purified by chromatography on silica gel eluting with DCM/MeOH (98:2 increasing in polarity to 95:5). The purified product was triturated with EtOAc to give the title compound (125 mg, 30%) as a solid. NMR: 1.39 (d, 6H), 2.48 (s, 3H), 3.12 (s, 3H), 4.68 (sept, 1H), 7.20 (s, 1H), 7.81 (d, 2H), 7.92 (d, 2H), 8.79 (s, 1H), 10.28 (br s, 1H); m/z 450.

Provenance & Evidence