1,4-diphenyl-1H-imidazole → 2-(1,4-diphenyl-1H-imidazol-2-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

HRID 1428948Notes

Reaction equation

C([Li])CCC.[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[CH:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:29][CH2:28]1)=[O:26].[Cl-].[NH4+].[Na]>C1COCC1>[C:6]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:13]2[CH2:24][C:25]([N:27]2[CH2:28][CH2:29][N:30]([C:33]3[N:34]=[CH:35][CH:36]=[CH:37][N:38]=3)[CH2:31][CH2:32]2)=[O:26])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

0.5 mL butyllithium (1.6 mol/L in THF) was added to 0.15 g 1,4-diphenyl-1H-imidazole in 10 mL THF at −78° C. under argon. The reaction was stirred 40 min at −78° C. and 0.22 g 2-bromo-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanon was added to the reaction. After stirring 1 h at −78° C. the reaction was decomposed with saturated sodiumammoniumchloride solution. The mixture was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5) to yield 20 mg of the desired compound. Rt: 1.13 (method B), (M+H)+: 425

Workup

stirringAfter stirring 1 h at −78° C. the reaction
extractionThe mixture was extracted with ethyl acetate
customThe organic layer was dried
customevaporated
customThe residue was purified by chromatography on Alox (gradient: dichlormethane/EtOAC/MeOH 9:2:0-50:45:5)

Sources & evidence

ORD record: ord-902ec9a6b65642d8829e509314723d0e
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937176B2

Reaction notes

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