Benzaldehyde → (5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)(phenyl)methanol

Participants

Reaction Steps

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (Example 1; 0.350 g, 0.930 mmol), MeLi (0.727 ml, 1.16 mmol), butyllithium (0.465 ml, 1.16 mmol), and benzaldehyde (0.0987 g, 0.930 mmol) were reacted according to Example 7 to provide (5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)(phenyl)methanol (0.182 g, 48.5% yield) after HCl salt formation. 1H NMR (DMSO-d6) δ 7.94 (s, 1H), 7.58 (s, 1H), 7.55 (d, 2H), 7.40-7.28 (m, 7H), 7.22 (m, 1H), 6.81 (s, 1H), 5.75 (s, 1H), 5.29 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=404.1 (M+H-HCl).

Provenance & Evidence