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

To a solution of 5,7-dichloropyrido[4,3-d]pyrimidin-4(3H)-one (2.16 g, 10 mmol) in dry DMF (50 mL) was added NaH (440 mg, 60% in mineral oil, 11 mmol) at 0° C. under N2. After the reaction mixture was allowed to warm to room temperature and stirred for 20 minutes, CH3I (0.75 mL, 1.7 g, 12 mmol) was added via syringe. The reaction mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was diluted with EtOAc (300 mL), washed with saturated NH4Cl solution (2×100 mL), water (50 mL) and brine (40 mL), and concentrated to result in a residue that was subjected to chromatography with gradient mixed solvents from hexanes/EtOAc (1:1) to (1:9) to afford the title compound. 1H NMR (DMSO-d6) 3.45 (s, 3H), 7.71 (s, 1H), 8.63 (s, 1H); ESI-MS m/z 230.0 (MH+).

1. stirringThe reaction mixture was stirred at room temperature for 18 hours
2. concentrationconcentrated under reduced pressure
3. additionThe residue was diluted with EtOAc (300 mL)
4. washwashed with saturated NH4Cl solution (2×100 mL), water (50 mL) and brine (40 mL)
5. concentrationconcentrated
6. customto result in a residue that

ORD record

ord-18cc6643a2f64694ac52ba0a4a6bf30e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354526B2