Potassium Carbonate → 3-(3-methoxybenzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

Participants

Reaction Steps

2-(4-Methylthiazol-2-ylamino)pyridin-3-ol (prepared according to Example 3, Step A) (0.150 g, 0.724 mmol), K2CO3 (0.225 g, 1.63 mmol), and 1-(chloromethyl)-3-methoxybenzene (0.113 g, 0.724 mmol) were reacted according to Example 3, Step B, to provide 3-(3-methoxybenzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.110 g, 46.4% yield). 1H NMR (CDCl3) δ 12.34 (bs, 1H), 7.93 (dd, 1H), 7.28 (d, 1H), 7.20 (m, 1H), 7.12 (m, 2H), 6.97 (m, 1H), 6.84 (m, 1H), 6.38 (s, 1H), 5.34 (s, 2H), 3.84 (s, 3H), 2.47 (s, 3H). Mass spectrum (apci) m/z=328.1 (M+H-HCl). Analysis calculated for C17H18N3O2ClS.0.54DCM: C, 56.29; H, 5.14; N, 11.23. found: C, 56.29; H, 5.23; N, 11.01.

Provenance & Evidence