HCID 67050500, compound → HCID 25214700, compound

HRID 2194754Notes

Reaction equation

HRID 2194754 reaction equation
[CH2:1]([N:5]1[C:10]([C:11]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][C:22]#[N:23])[CH:16]=[C:17]([CH3:19])[CH:18]=2)=[O:12])=[C:9]([CH:24]([CH3:26])[CH3:25])[C:8](=[O:27])[NH:7][C:6]1=[O:28])[CH2:2][CH2:3][CH3:4]>[Pd].C(O)C>[CH2:1]([N:5]1[C:10]([C:11]([C:13]2[CH:14]=[C:15]([CH2:20][CH2:21][C:22]#[N:23])[CH:16]=[C:17]([CH3:19])[CH:18]=2)=[O:12])=[C:9]([CH:24]([CH3:25])[CH3:26])[C:8](=[O:27])[NH:7][C:6]1=[O:28])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 67050500HCID 67050500, compound2×

Product 1

HCID 25214700HCID 25214700, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-[3-(3-Butyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (Compound 74) (180 mg, 0.474 mmol) was stirred with 10% palladium on carbon (20 mg) in anhydrous ethanol (10 mL) at room temperature under an atmosphere of hydrogen. After 17 hr., the reaction mixture was filtered through a celite pad and the pad was washed with ethanol and chloroform. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 120 mg (66%) of 3-[3-(3-butyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-propionitrile (76) as a white foam. Recrystallization from ether-hexane resulted in a white solid. m.p. 172-173° C.; 1H-NMR (300 MHz, CDCl3) δ 0.79 (3H, t, J=7.5 Hz), 1.12-1.24 (8H, m), 1.45-1.59 (2H, m), 2.30 (1H, m), 2.46 (3H, s), 2.68 (2H, t, J=7.2 Hz), 3.00-3.15 (3H, m), 3.79 (1H, m), 7.44 (1H, s), 7.63 (2H, s), 8.89 (1H, s); m/z (EI) 381 (M+).

Workup

  1. filtration, the reaction mixture was filtered through a celite pad
  2. washthe pad was washed with ethanol and chloroform
  3. customThe combined filtrate was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Sources & evidence

ORD record
ord-80e4b554288c47079c6afbb8cc9baac0
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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