2-Iodo-2-methylpropane → HCID 25214952, 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) (1.19 g, 4 mmol) and powdered anhydrous potassium carbonate (662 mg, 4.8 mmol) in DMF (20 mL), was added 2-iodo-2-methylpropane (460 μL, 4 mmol). The mixture was then stirred in an oil bath (50-60° C.) for overnight and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 500 mg (35%) of 3-(3-isobutyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (78) as a white solid. m.p. 200-201° C.; 1H-NMR (200 MHz, CDCl3) δ 0.80 (3H, d, J=3.2 Hz), 0.83 (3H, d, J=3.2 Hz), 1.12 (3H, d, J=7.0 Hz), 1.23 (3H, d), J=7.0 Hz), 1.90 (1H, m), 2.25 (1H, m), 2.53 (3H, s), 2.93 (1H, dd, J=14.2 Hz, J=7.4 Hz), 3.75 (1H, dd, J=14.2 Hz, J=7.4 Hz), 7.80 (1H, s), 7.92 (1H, s), 8.03 (1H, s), 9.03 (1H, s); m/z (EI) 353 (M+).

Provenance & Evidence