3-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile → 3-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-pyrimidine-4-carbonyl)-5-methyl-phenyl]propanenitrile

HRID 2194753Notes

Reaction equation

HRID 2194753 reaction equation
[CH2:1]([N:3]1[C:8]([C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:20]#[N:21])[CH:14]=[C:15]([CH3:17])[CH:16]=2)=[O:10])=[C:7]([CH:22]([CH3:24])[CH3:23])[C:6](=[O:25])[NH:5][C:4]1=[O:26])[CH3:2]>[Pd].C(O)C>[CH2:1]([N:3]1[C:8]([C:9]([C:11]2[CH:12]=[C:13]([CH2:18][CH2:19][C:20]#[N:21])[CH:14]=[C:15]([CH3:17])[CH:16]=2)=[O:10])=[C:7]([CH:22]([CH3:23])[CH3:24])[C:6](=[O:25])[NH:5][C:4]1=[O:26])[CH3:2]

Participants

4

Reactant 1

HCID 670505193-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile2×

Product 1

HCID 252146993-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-pyrimidine-4-carbonyl)-5-methyl-phenyl]propanenitrileYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-[3-(3-Ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (Compound 73) (190 mg, 0.54 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 180 mg (94%) of 3-[3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-propionitrile (75) as a white foam. Recrystallization from chloroform-ether resulted in a white solid. m.p. 173-174° C.; 1H-NMR (300 MHz, CDCl3) δ 1.13-1.18 (6H, m), 1.23 (3H, d, J=6.9 Hz), 2.31 (1H, m), 2.47 (3H, s), 2.70 (2H, t, J=6.9 Hz), 3.04 (2H, t, J=6.9 Hz), 3.25 (1H, m), 3.89 (1H, m), 7.45 (1H, s), 7.66 (2H, s), 9.17 (1H, s); m/z (EI) 353 (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-2aef2f63d61447c982680d3a1d5a7baf
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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