Potassium Carbonate → 3-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

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Reaction Steps

Following the method according to Example 3, Steps B and C, 5, 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (prepared according to Example 3, Step A; 5.0 g, 24 mmol), (3-(bromomethyl)phenoxy)(tert-butyl)dimethylsilane (7.3 g, 24 mmol) [J. Med. Chem. (1992), 35, 3498] and potassium carbonate (8.3 g, 60 mmol) were combined to provide 3-(3-(tert-butyldimethylsilyloxy)benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (5.4 g, 48% yield) as a clear and colorless oil. 1H NMR (CDCl3) δ 8.61 (bs, 1H), 7.94 (dd, 1H), 7.26 (m, 1H), 7.06 (dd, 1H), 7.00 (m, 1H), 6.84 (m, 2H), 6.79 (dd, 1H), 6.38 (s, 1H), 5.06 (s, 2H), 2.33 (s, 3H), 0.97 (s, 9H), 0.20 (s, 6H). Mass spectrum (apci) m/z=428.2 (M+H).

Provenance & Evidence