HCID 18925251, compound → HCID 54059613, compound

HRID 2194814Notes

Reaction equation

HRID 2194814 reaction equation
[CH2:1]([N:5]1[C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=2)=[C:9]([CH:20]([CH3:22])[CH3:21])[C:8](=[O:23])[NH:7][C:6]1=[O:24])[C:2]#[C:3][CH3:4]>CO.[Pd]>[CH2:1]([N:5]1[C:10]([O:11][C:12]2[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=2)=[C:9]([CH:20]([CH3:21])[CH3:22])[C:8](=[O:23])[NH:7][C:6]1=[O:24])[CH:2]=[CH:3][CH3:4]

Participants

4

Reactant 1

HCID 18925251HCID 18925251, compound

Product 1

HCID 54059613HCID 54059613, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-But-2-ynyl-6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (116) (50 mg, 0.15 mmol) was stirred in the presence of palladium on barium sulfate (15 mg) in methanol (5 mL) under a hydrogen atmosphere. After 15 min., the mixture was filtered through a plug of celite and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2)) to afford 50 mg (100%) of a white solid. m.p. 141-142° C.; 1H-NMR (200 MHz, CDCl3) δ 1.13 (6H, d, J=7.0 Hz), 1.61 (3H, dd, J=6.9 Hz, 1.4 Hz), 2.31 (6H; s), 2.79 (1H, m), 4.35 (2H, d, J=6.8 Hz), 5.38 (1H, m), 5.60 (1H, m), 6.54 (2H, s), 6.77 (1H, s); m/z (EI) 328(M+).

Workup

  1. filtrationthe mixture was filtered through a plug of celite
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:2))

Sources & evidence

ORD record
ord-595526c71cfb461f8facea1fe95a06da
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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