Stannous Chloride → HCID 59627820, compound

Participants

Reaction Steps

A suspension of 2-chloro-5-nitro-N-(quinolin-6-ylmethyl)pyrimidin-4-amine (2.25 g, 7.14 mmol), SnCl2 (7.18 g, 32 mmol) in ethanol (50 mL) and CHCl3 (10 mL) was refluxed for 5 h. The mixture was allowed to cool to room temperature and the solvent was evaporated. The residue was basified to pH 10 by saturated aqueous NaHCO3. The resulting suspension was stirred in ethanol (500 mL) for 2 h and filtered through a pad of silica gel. The filtrate was evaporated. Flash chromatography of the residue over silica gel, using 100% EtOAc to 10% MeOH-EtOAc with 0.5% NH3H2O, gave the desired product (1.02 g, 50%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 4.88 (s, 2H), 7.46-7.53 (m, 2H), 7.77-8.02 (m, 3H), 8.32 (d, 1H, J=8.0 Hz), 8.8 (m, 1H); LCMS (APCI) m/z 286.2 (M+H+).

Provenance & Evidence