Dimethyl Disulfide → 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 0.250 g, 0.664 mmol) was added to THF (30 mL) and cooled to −78° C. MeLi (0.519 mL, 0.831 mmol) was slowly added, and the reaction mixture was stirred for 10 minutes. Butyllithium (0.332 mL, 0.831 mmol) was added, and the reaction mixture was stirred for 15 minutes. 1,2-Dimethyldisulfane (0.438 g, 4.65 mmol) was added, and the reaction mixture was stirred for 15 minutes. Ammonium chloride was added, and the reaction mixture was extracted with CH2Cl2. The organic layer was purified by silica gel (10-20% EtOAc in hexanes) to give 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(methylthio)pyridin-2-amine (0.170 g, 74.5% yield). A portion of this compound was dissolved in dichloromethane, 2M HCl in ether was added, and the mixture was concentrated to give the title compound. 1H NMR (CDCl3) δ 12.30 (bs, 1H), 7.84 (m, 1H), 7.57 (d, 2H), 7.39 (m, 2H), 7.32 (m, 1H), 7.15 (m, 1H), 6.38 (s, 1H), 5.35 (s, 2H), 2.45 (s, 3H), 2.43 (s, 3H). Mass spectrum (apci) m/z=344.0 (M+H-HCl).

Provenance & Evidence