Ethanol → 3-(Benzyloxy)-N-(4-Methyl-1,3-Thiazol-2-Yl)pyridin-2-Amine

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Reaction Steps

A 1 L round-bottomed flask was charged with 1-(3-(benzyloxy)pyridin-2-yl)thiourea (31.7 g, 122 mmol), triethylamine (29.0 mL, 207 mmol), 1-chloropropan-2-one (13.6 mL, 171 mmol), and EtOH (400 mL). The reaction mixture was heated to reflux overnight, then poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (32.7 g, 89.9% yield) as a yellow solid. 1H NMR (CDCl3) δ 8.58 (s, 1H), 7.93 (m, 1H), 7.39 (m, 5H), 7.08 (d, 1H), 6.80 (dd, 1H), 6.37 (s, 1H), 5.08 (s, 2H), 2.32 (s, 3H). LCMS (25 to 95) Rt=2.94 min (apci) m/z=298 (M+H).

Provenance & Evidence