Sodium Bicarbonate → 2-(4-Methylthiazol-2-ylamino)pyridin-3-ol

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Reaction Steps

A 250 mL round-bottomed flask was charged 3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (11.4 g, 38.3 mmol) in 6M HCl (100 mL), and the reaction mixture was heated to reflux for 10 hours. The reaction mixture was cooled to room temperature, poured onto ice and saturated sodium bicarbonate, filtered, dried under vacuum and triturated with hexanes to afford 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (6.23 g, 78.5% yield) as a pale yellow solid. 1H NMR (CD3OD) δ 7.79 (dd, 1H), 7.07 (dd, 1H), 6.79 (dd, 1H), 6.46 (q, 1H), 2.28 (s, 3H). LCMS (5 to 95) Rt=2.69 min (apci) m/z=208 (M+H).

Provenance & Evidence