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

HRID 1851171Notes

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, 5.6 mg Zn, 63.7 mg Zn(CN)2 and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct were suspended in dimethylacetamide and the mixture was heated for 45 min under microwave irradiation to 160° C. The workup was performed by diluting the mixture with water and dichlormethane, extracting the aqueous layer twice and drying the combined organic layers over Na2SO4. The compound was 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 was isolated by evaporation of the solvent and chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record: ord-7b93749c13cc4196b23fc169f9802bea
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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