3-(2,6-Bis-benzyloxy-5-ethyl-pyrimidine-4-carbonyl)-5-methyl-benzonitrile → 3-(5-ethyl-2,4-dioxo-1H-pyrimidine-6-carbonyl)-5-methyl-benzonitrile

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Reaction Steps

3-(2,6-Bis-benzyloxy-5-ethyl-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (41) (4.5 g, 9.7 mmol) in anhydrous ethanol (30 ml) and THF (30 ml) was stirred with 10% palladium on carbon (250 mg) under an atmosphere of hydrogen. After 1.5 hr, the mixture was filtered through celite pad and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, chloroform:methanol (95:5)) to afford 20.3 g (84%) of a white solid; m.p. 253-254° C.; 1H NMR (200 MHz, DMSO-d6) δ: 0.84 (3H, t, J=7.0 Hz), 1.96 (2H, q, J=7.0 Hz), 2.45 (3H, s), 8.06 (1H, s), 8.11 (1H, s), 8.33 (1H, s), 11.05 (1H, s), 8.28 (1H, s); m/z (EI): 283 (M+).

Provenance & Evidence