Dimethyl Sulfoxide → 6-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-one

HRID 1291385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291385
[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][NH:12][C:6]2=[N:5][C:4]=1[CH3:13])[CH3:2].[Si]([O:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CN(C=O)C>[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:32][C:31]3[CH:30]=[CH:29][C:28]([C:26](=[O:27])[C:25]4[CH:36]=[CH:37][C:22]([OH:21])=[CH:23][CH:24]=4)=[CH:35][CH:34]=3)[C:6]2=[N:5][C:4]=1[CH3:13])[CH3:2]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 18918912HCID 18918912, VerbindungHCID 178436760HCID 178436760, Verbindung

Produkt 1

HCID 189189466-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-oneAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-ethyl-7-methylimidazo[1,2-a]-pyrimidin-5(1H)-one (3.93 g), 4-(4-t-butyldimethylsilyloxybenzoyl)benzyl bromide (14.79 g) and potassium carbonate (5.97 g) in DMF (25 ml)-dimethyl sulfoxide (25 ml) was stirred at room temperature for 20 hours. This reaction mixture was concentrated and the residue was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1) and recrystallized from ethanol-ethyl acetate to provide the title compound as colorless solid (909 mg).

Aufarbeitung

  1. concentrationThis reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (dichloromethane: methanol =9:1)
  7. customrecrystallized from ethanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ce19d69685834beca3632b89a35c6d89
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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