4-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde → 1-[4-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)phenyl]ethanol

HRID 1851237Notes

Reaction equation

[C:1]1([C:7]2[C:8]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][Zn]Cl>C1COCC1>[C:1]1([C:7]2[C:8]([C:16]3[CH:17]=[CH:18][C:19]([CH:20]([OH:21])[CH3:24])=[CH:22][CH:23]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

100 mg 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde (prepared as described for example 1) were dissolved in 2 mL THF and 1 mL of a 2M solution of MeZnCl was added. The mixture was heated (100° C., microwave) for 2 h, cooled to room temperature and extracted with a mixture of dichloromethane and water. The organic layers were dried over sodium sulphate and the solvent was evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Workup

temperaturecooled to room temperature
extractionextracted with a mixture of dichloromethane and water
dry with materialThe organic layers were dried over sodium sulphate
customthe solvent was evaporated
customThe crude product was purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record: ord-744e175ee2f5452bac3f3f135ef85d16
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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