Isopropyl iodide → HCID 25214953, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (5.94 g, 20 mmol) and powdered anhydrous potassium carbonate (3.31 g, 24 mmol) in DMF (40 mL), was added 2-iodopropane (2 mL, 20 mmol). The mixture was then stirred in an oil bath (50-60° C.) overnight and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 700 mg (10%) of 3-(3,5-diisopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (77) as a white solid. m.p. 278-280° C.; 1H-NMR (200 MHz, CDCl3) δ 1.11 (3H, d, J=7.0 Hz), 1.20 (3H, d, J=7.0 Hz), 1.37 (3H, d, J=6.6 Hz), 1.47 (3H, d, J=6.6 Hz), 2.19 (1H, m), 2.54 (3H, s), 3.55 (1H, m), 7.81 (1H, s), 7.98 (1H, s), 8.07 (1H, s), 9.09 (1H, s); m/z (EI) 339 (M+).

Provenance & Evidence