Stannous chloride dihydrate → 4,6-Dichloro-2-(methylsulfanyl)pyrimidin-5-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,6-dichloro-2-methylsulfanyl-5-nitro-pyrimidine (1.0 g, 4.2 mmol) in EtOH (20 mL) was added SnCl2.2H2O (3.8 g, 17 mmol). The mixture was heated to 90° C. After 2 h, the reaction mixture was cooled and the solution was concentrated. The residue was treated with saturated (satd.) aqueous (aq.) NaHCO3 until pH 8. The resulting mixture was then extracted with EtOAc (3×100 mL). The combined organic extracts were dried, filtered, and concentrated. The residue was purified by FCC to afford a colorless solid (723 mg, 87%). MS (ESI): mass calcd. for C5H5Cl2N3S, 208.9; m/z found, 210.3 [M+H]+. 1H NMR ((CD3)2SO): 5.89 (s, 2H), 2.45 (s, 3H).

Provenance & Evidence