Dimethylacetamide → 7-(4-Formylphenyl)-6-phenylimidazo[1,2-a]pyrimidine-3-carbonitrile

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Reaktionsgleichung

Br[C:2]1[N:6]2[CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[N:10][C:5]2=[N:4][CH:3]=1.C[C:26]([N:28](C)C)=O>O.ClCCl.[Zn].[C-]#N.[C-]#N.[Zn+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:15]([C:14]1[CH:17]=[CH:18][C:11]([C:9]2[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:7][N:6]3[C:2]([C:26]#[N:28])=[CH:3][N:4]=[C:5]3[N:10]=2)=[CH:12][CH:13]=1)=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

350 mg 4-(3-bromo-6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde (prepared as described in example 11), 5.6 mg Zn, 63.7 mg Zn(CN)2 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct are suspended in dimethylacetamide and the mixture is heated for 45 min under microwave irradiation to 160° C. The workup is performed by diluting the mixture with water and dichlormethane, extracting the aqueous layer twice and drying the combined organic layers over Na2SO4. The compound is isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/methanol).

Aufarbeitung

extractionextracting the aqueous layer twice
dry with materialdrying the combined organic layers over Na2SO4
customThe compound is isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag: ord-34da83e5067441869f75787894a31603
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07776864B2

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