Dimethylformamide → HCID 18510765, compound

Participants

Reaction Conditions

Reaction Steps

1-Chloro-2,4-pyrrolidinedione (0.011 mol; 98%) was added portionwise to a solution of 5-pyrimidinecarboxaldehyde, oxime (0.036 mol) in DMF (50 ml) and this mixture was heated to 50° C. to start the reaction. The mixture was cooled to RT. Pyridine (0.28 ml) was added. The rest of 1-chloro-2,4-pyrrolidinedione (0.043 mol) was added portionwise and the mixture was stirred for 3 hours at RT. N-(4-benzoylphenyl)-propenamide (0.025 mol) was added. Triethylamine (0.053 mol) was added dropwise and the resulting reaction mixture was stirred overnight at RT. The crude mixture was washed with water, then extracted with EtOAc. The organic layer was separated, and the solvent was evaporated. The residue was washed with water and extracted with CH2Cl2. The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated. The residue was crystallized from CH3OH, washed with diethyl ether and hot CH2Cl2, dried and repurified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 97/3). The pure fractions were collected and the solvent was evaporated, yielding 3.5 g of (±)-N-(4-benzoylphenyl)-4,5-dihydro-3-(5-pyrimidinyl)-5-isoxazolecarboxamide (compound 349)

Provenance & Evidence