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

HRID 426120Notes

Reaction equation

HRID 426120 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=2)[C:20]#[N:21])=[O:16])[C:12]([CH2:26][CH3:27])=[C:11]([O:28]CC2C=CC=CC=2)[N:10]=1)C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[CH2:26]([C:12]1[C:11](=[O:28])[NH:10][C:9](=[O:8])[NH:14][C:13]=1[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:20]#[N:21])=[O:16])[CH3:27]

Participants

5

Reactant 1

HCID 591847853-(2,6-Bis-benzyloxy-5-ethyl-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 596868563-(5-ethyl-2,4-dioxo-1H-pyrimidine-6-carbonyl)-5-methyl-benzonitrileYield 738.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  1. filtrationthe mixture was filtered through celite pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent, chloroform:methanol (95:5))

Sources & evidence

ORD record
ord-6fb824d0be97411db0a53e7a96601e44
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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