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

HRID 1915534Notes

Reaction equation

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]

Participants

Conditions

Temperature: 160 °C

Procedure

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).

Workup

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)

Sources & evidence

ORD record: ord-b90b9f52adf845508d5882ed1fcc4ee8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614218B2

Reaction notes

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