Benzenamine, 4-(1-methylpropyl)- → HCID 58532510, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of acetic acid 2,6-dimethyl-4-(4-oxo-4H-pyrido[4,3-d][1,3]oxazin-2-yl)-phenyl ester (1.04 g, 3.35 mmol) in glacial acetic acid (20 mL) was added 4-(sec-butyl)-aniline (B) (0.750 g, 5.02 mmol). The reaction mixture was stirred at 120° C. for 60 hours under nitrogen and cooled to room temperature. Acetic acid was removed under reduced pressure. The residue was diluted with water (100 mL), neutralized to pH 7 with saturated aqueous NaHCO3 solution, and extracted with ethyl acetate (200 mL). The organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Solvent was evaporated and the crude compound was purified by column chromatography (silica gel 230-400 mesh; 20-30% ethyl acetate in hexanes as eluent) to give acetic acid 4-[3-(4-sec-butyl-phenyl)-4-oxo-3,4-dihydro-pyrido[4,3,d]pyrimidin-2-yl]-2,6-dimethyl-phenyl ester (7) as a white solid. Yield: 0.580 g (39%).

Provenance & Evidence