4-(6-Phenyl-3-vinylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde → 4-(3-Ethyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

HRID 1851192Notes

Reaction equation

HRID 1851192 reaction equation
[C:1]1([C:7]2[C:8]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)=[N:9][C:10]3[N:11]([C:13]([CH:16]=[CH2:17])=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.CCO.[Pd]>[CH2:16]([C:13]1[N:11]2[CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)=[N:9][C:10]2=[N:15][CH:14]=1)[CH3:17]

Participants

5

Reactant 1

HCID 866306634-(6-Phenyl-3-vinylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 866306664-(3-Ethyl-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg 4-(6-phenyl-3-vinylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde (prepared as described under intermediate example 13) were dissolved in a mixture of 5 mL THF and 5 mL EtOH. 10 mg 10% Pd/C were added and the mixture stirred under an atmosphere of hydrogen for 2 h. The mixture was filtered through Celite, the solvent was evaporated and the crude product was purified by chromatography on silica gel (dichloromethane/methanol).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was evaporated
  3. customthe crude product was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-743b0d8fdee04930b035e89f4d4fb9a7
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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