Ethanol → 2,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pentan-1-one

HRID 1677516Notes

Reaction equation

HRID 1677516 reaction equation
[CH3:1][C:2]([CH3:29])([CH2:26][CH:27]=[CH2:28])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4].C(O)C>[Pd].CO>[CH3:1][C:2]([CH3:29])([CH2:26][CH2:27][CH3:28])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 702EthanolHCID 59540666HCID 59540666, compound

Product 1

HCID 595407802,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pentan-1-oneYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pent-4-en-1-one (0.036 g, 0.091 mmol), 3 mL of ethanol (a small amount of methanol was also added to help solubility) and 10% Pd/C (10 mg) was stirred under a hydrogen atmosphere (balloon) for 3 d, then filtered through Celite and concentrated to afford 0.019 g (53%) of 2,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pentan-1-one as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c3796db7fc85409388b72626cf8bcec8
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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