Water → 2-(4-Bromo-2-phenyl-imidazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone

HRID 84772Notes

Reaction equation

C([Li])CCC.[Br:6][C:7]1[N:8]=[C:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:10]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])[C:11]=1Br.O>C1COCC1>[Br:6][C:7]1[N:8]=[C:9]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:10]([CH2:13][C:14]([N:16]2[CH2:17][CH2:18][N:19]([C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:20][CH2:21]2)=[O:15])[CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

9.4 mL 2.5 mol/L butyllithium solution in THF was added dropwise to 11.8 g 2-(4,5-dibromo-2-phenyl-imidazol-1-yl)-1-(4-pyrimidin-2-yl-piperazin-1-yl)-ethanone in 150 mL THF at −78° C. under argon. The reaction mixture was stirred 2 h at −78° C. followed by careful and dropwise addition of water to the mixture. The resulting mixture was stirred 30 min at −78° C. and then again water was added at 0° C. The mixture was extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified chromatoraphie on silica (petrolether 1/ethylacetate 1). Diisopropylether was added to the residue and the precipitate was filtered and dried to give 1.7 g desired product. Rt: 0.94 (method B), ESI+: 427

Workup

stirringThe resulting mixture was stirred 30 min at −78° C.
extractionThe mixture was extracted with ethyl acetate
customThe organic layer was dried
customevaporated
customThe residue was purified chromatoraphie on silica (petrolether 1/ethylacetate 1)
additionDiisopropylether was added to the residue
filtrationthe precipitate was filtered
customdried

Sources & evidence

ORD record: ord-0c3eb6c35c8749d4957a39783857db7a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846948B2

Reaction notes

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