Potassium Carbonate → 3-[3-(3-Cyclopropylmethyl-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), anhydrous powdered potassium carbonate (165 mg, 1.2 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 mL) at room temperature, was added bromomethyl cyclopropane (97 μL, 1 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 320 mg (84%) of 3-[3-(3-cyclopropylmethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (72) as a white solid. The product was recrystallized from chloroform-ether to afford a white solid. m.p. 225-226° C.; 1H-NMR (300 MHz, CDCl3) δ 0.22-0.44 (4H, m), 0.93 (1H, m), 1.12 (3H, d, J=6.9 Hz), 1.24 (3H, d, J=6.9 Hz), 2.28 (1H, m), 2.50 (3H, s), 3.28 (1H, dd, J=6.0 Hz, J=15.0 Hz), 3.59 (1H, dd, J=6.0 Hz, J=15.0 Hz), 6.01 (1H, d, J=16.8 Hz), 7.44 (1H, d, J=16.8 Hz), 7.61 (1H, s), 7.77 (1H, s), 7.88 (1H, s), 9.00 (1H, s); m/z (EI) 377 (M+).

Provenance & Evidence