Methanol → 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5,7-dichloropyrido[4,3-d]pyrimidin-4(3H)-one (1.73 g, 8.0 mmol) in dry DMF (25 mL) was added NaH (352 mg, 60% in mineral oil, 8.8 mmol) at 0° C. and the resulting mixture was stirred under N2 at 0° C. for 30 min. MeI (0.6 mL, 1.36 g, 9.6 mmol) was added via a syringe and the reaction mixture was stirred at room temperature for 14 hours and was cooled to 0° C. MeOH (2.0 mL) was added slowly and the reaction mixture was stirred for 20 minutes at room temperature and then concentrated under reduced pressure. The resulting residue was partitioned between 10% aqueous NH4Cl solution (80 mL) and EtOAc (40 mL). The aqueous phase was separated and extracted with EtOAc (3×30 mL). The combined EtOAc extracts were washed with brine (8 mL), dried over MgSO4 and evaporated to afford the title compound. 1H NMR (DMSO-d6) δ 3.46 (s, 3H), 7.74 (s, 1H), 8.64 (s, 1H); ESI-MS m/z 230.1 (MH+).

Provenance & Evidence