HCID 67050500, compound → HCID 25214700, compound

Participants

Reaction Steps

3-[3-(3-Butyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (Compound 74) (180 mg, 0.474 mmol) was stirred with 10% palladium on carbon (20 mg) in anhydrous ethanol (10 mL) at room temperature under an atmosphere of hydrogen. After 17 hr., the reaction mixture was filtered through a celite pad and the pad was washed with ethanol and chloroform. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 120 mg (66%) of 3-[3-(3-butyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-propionitrile (76) as a white foam. Recrystallization from ether-hexane resulted in a white solid. m.p. 172-173° C.; 1H-NMR (300 MHz, CDCl3) δ 0.79 (3H, t, J=7.5 Hz), 1.12-1.24 (8H, m), 1.45-1.59 (2H, m), 2.30 (1H, m), 2.46 (3H, s), 2.68 (2H, t, J=7.2 Hz), 3.00-3.15 (3H, m), 3.79 (1H, m), 7.44 (1H, s), 7.63 (2H, s), 8.89 (1H, s); m/z (EI) 381 (M+).

Provenance & Evidence