3-(2,6-Bis-benzyloxy-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile → 3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrile

HRID 426146Notes

Reaction equation

HRID 426146 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH:21]=[C:22]([CH3:24])[CH:23]=2)[C:19]#[N:20])[C:12]([CH:25]([CH3:27])[CH3:26])=[C:11]([O:28]CC2C=CC=CC=2)[N:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH:25]([C:12]1[C:11](=[O:28])[NH:10][C:9](=[O:8])[NH:14][C:13]=1[O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:19]#[N:20])([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 591846633-(2,6-Bis-benzyloxy-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzonitrile

Product 1

HCID 596868373-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzonitrileYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Compound (72) (2.89 g) in anhydrous ethanol (30 ml) was stirred with 10% palladium on carbon (300 mg) under an atmosphere of hydrogen. After 6 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, dichloromethane:methanol (95:5)) to afford 1 g of the title compound as a white solid. m.p. 272-275° C.; 1H NMR (200 MHz, DMSO-d6) δ 1.06 (6H, d, J=7.4 Hz), 2.36 (3H, s), 2.78 (1H, m), 7.33 (1H, s), 7.45 (1H, s), 7.55 (1H, s), 11.05 (1H, s), 11.34 (1H, s); m/z (EI) 285 (M+).

Workup

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

Sources & evidence

ORD record
ord-55a387f8f8a746d89dba79d8e8ab43a6
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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