3-{3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-phenyl}-acrylonitrile → 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-phenyl]-acrylonitrile
Reaction equation
[CH:1]([C:4]1[C:5]([C:30]([C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][C:40]#[N:41])[CH:35]=[CH:36][CH:37]=2)=[O:31])=[N:6][C:7]([O:20]CC2C=CC(OC)=CC=2)=[N:8][C:9]=1[O:10]CC1C=CC(OC)=CC=1)([CH3:3])[CH3:2]>C(#N)C>[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:20])[NH:6][C:5]=1[C:30]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]#[N:41])[CH:35]=[CH:36][CH:37]=1)=[O:31])([CH3:3])[CH3:2]Participants
3
Procedure
To a stirred solution of 3-{3-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-phenyl}-acrylonitrile (1.25 g, 2.23 mmol) in acetonitrile (10 ml) at room temperature, was added ceric ammonium nitrate (3.67 g, 6.70 mmol) followed by distilled water (5 ml). After 3 hr., the reaction mixture was diluted with EA, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a white solid. The crude product was purified by silica gel column chromatography (eluent, EA:hexanes (4:1)) to afford 240 mg (35%) of a white solid. m.p. 210-211° C.; 1H NMR (200 MHz, CD3OD/CDCl3) δ 1.10 (6H, d, J=6.8 Hz), 2.39 (1H, m), 6.03 (1H, d, J=16.8 Hz), 7.45 (1H, d, J=16.8 Hz), 7.58 (3H, m), 8.01 (1H, s); m/z (LC/Mass, EI) 310 (M+H+).