Iodoethane → 3-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

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Reaction Steps

To a stirred solution of 3-[3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (Compound 55) (323 mg, 1 mmol) and anhydrous powdered potassium carbonate (165 mg, 1.2 mmol) in DMF at room temperature, was added iodoethane (97 μL, 1.2 mmol). After stirring overnight, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to give 190 mg (54%) of 3-[3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (73) as a white solid. The product was recrystallized from chloroform-ether. m.p. 174-176° C.; 1H-NMR (200 MHz, CDCl3) δ 1.12-1.30 (9H, m), 2.29 (1H, m), 2.51 (3H, s), 3.25 (1H, m), 3.90 (1H, m), 6.06 (1H, d, J=16.8 Hz), 7.47 (1H, d, J=16.8 Hz), 7.64 (1H, s), 7.80 (1H, s), 7.92 (1H, s), 10.08 (1H, s); m/z (EI) 351 (M+).

Provenance & Evidence