Benzoyl chloride → HCID 86723526, compound

Participants

Reaction Steps

1,3-Diethyl-6-methylpyrimidine-2,4(1H,3H)-dione (step 1)(680 mg, 3.73 mmol), benzoyl chloride (1.299 mL, 11.20 mmol) and tin(IV) chloride (1.314 mL, 11.20 mmol) were combined in chlorobenzene (30 mL, 295 mmol) and the mixture heated at reflux for 16 h. The reaction mixture was cooled to RT and diluted with EtOAc. The mixture was washed with 2M NaOH(aq) until basic. The organic phase was washed with brine, dried over sodium sulphate and evaporated under vacuum. The residue was dissolved in DCM and evaporated onto silica. The silica was deposited onto a 10 g silica cartridge and the system eluted with 10% EtOAc/hexane, 20% EtOAc/hexane, 40% EtOAc/hexane and 50% EtOAc/hexane. Product elutes at 40% EtOAc/hexane. Fractions were concentrated under vacuum to yield the title compound as an off white solid;

Provenance & Evidence