HCID 22024450, compound → HCID 22024467, compound

HRID 501021Notes

Reaction equation

HRID 501021 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[C:11]1[C:12]2[N:13]([C:17](/[C:22](/[CH2:26][CH2:27][CH3:28])=[CH:23]\[CH2:24][CH3:25])=[C:18]([CH2:20][CH3:21])[N:19]=2)[CH:14]=[CH:15][N:16]=1>C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[C:11]1[C:12]2[N:13]([C:17]([CH:22]([CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH3:28])=[C:18]([CH2:20][CH3:21])[N:19]=2)[CH:14]=[CH:15][N:16]=1

Participants

4

Reactant 1

HCID 22024450HCID 22024450, compound

Product 1

HCID 22024467HCID 22024467, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

2-[2-Ethyl-3-[(Z)-1-propyl-1-butenyl]imidazo[1,2-a]pyrazin-8-yl]-3,5-dimethylphenyl methyl ether (41 mg, 0.12 mmol) was dissolved in ethanol (1.5 mL), then 10% palladium-carbon (50% hydrous product; 120 mg) was added thereto, and the mixture was heated under stirring at 45° C. for 4 hours at a normal pressure under hydrogen atmosphere. The mixture was further stirred at room temperature for 15 hours. The reaction mixture was filtered and washed with ethyl acetate, and then the filtrates were combined and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to give the title compound (25 mg) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. stirringThe mixture was further stirred at room temperature for 15 hours
  3. filtrationThe reaction mixture was filtered
  4. washwashed with ethyl acetate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-9d6f9a2da0004d57bdf3f98686324f52
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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