2-Amino-3-benzyloxypyridine → HCID 59225647, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-3-isothiocyanatopyridine (0.342 g, 2.00 mmol) and 3-(benzyloxy)pyridin-2-amine (0.401 g, 2.00 mmol) in ethylene glycol (2 mL) was heated at 120° C. for 3 hours. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by MPLC eluting with 4:1 hexane:ethyl acetate to afford the title compound as a wax. The wax was triturated with 10:1 hexanes:dichloromethane (11 mL), filtered, and dried to afford N-(3-(benzyloxy)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine (0.095 g, 14.2% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 5.30 (s, 2H), 7.03 (m, 1H), 7.32-7.43 (m, 4H), 7.50 (d, 1H), 7.60 (d, 2H), 7.93-7.97 (m, 2H), 8.35 (d, 1H), 10.71 (s, 1H).

Provenance & Evidence