Triethylamine → N-(3-(Benzyloxy)-5-bromopyridin-2-yl)-4,5-dimethylthiazol-2-amine hydrochloride

Participants

Reaction Steps

A mixture of 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (0.50 g, 1.48 mmol), 3-chlorobutan-2-one (0.236 g, 2.22 mmol), triethylamine (0.412 ml, 2.96 mmol), and ethanol (15 mL) was heated overnight. The reaction mixture was cooled, partitioned between ethyl acetate and water, washed with water and brine, dried, and concentrated. The residue was purified by MPLC eluting with 5:1 hexane:ethyl acetate to afford the free base of the title compound (104 mg) as a tacky oil. The free base was dissolved in ether (4 mL) and a 1M solution of HCl in ether was added (1.5 mL). The mixture was stirred 10 minutes and filtered. The solids were washed with ether, hexanes, and dried to afford 3-(benzyloxy)-5-bromo-N-(4,5-dimethylthiazol-2-ylpyridin-2-amine hydrochloride (0.093 g, 14.7% yield). 1H NMR (DMSO-d6) δ 2.21 (s, 3H), 2.26 (s, 3H), 5.34 (s, 2H), 7.35-7.44 (m, 3H), 7.58 (d, 2H), 7.81 (s, 1H), 8.05 (s, 1H).

Provenance & Evidence