Potassium Carbonate → 6-Ethyl-7-methyl-1-[4-[4-(4-picolyloxy)benzoyl]-benzyl]imidazo[1,2-a]pyrimidin-5(1H)-one hydrochloride

HRID 1291386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291386
[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:28])[C:21]4[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:6]2=[N:5][C:4]=1[CH3:29])[CH3:2].Cl.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][Cl:38])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:38].[CH2:1]([C:3]1[C:8](=[O:9])[N:7]2[CH:10]=[CH:11][N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:28])[C:21]4[CH:22]=[CH:23][C:24]([O:27][CH2:37][C:34]5[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=5)=[CH:25][CH:26]=4)=[CH:16][CH:15]=3)[C:6]2=[N:5][C:4]=1[CH3:29])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 189189466-Ethyl-1-[4-(4-hydroxybenzoyl)benzyl]-7-methyl-imidazo[1,2-a]pyrimidin-5(1H)-one

Produkt 1

HCID 189192606-Ethyl-7-methyl-1-[4-[4-(4-picolyloxy)benzoyl]-benzyl]imidazo[1,2-a]pyrimidin-5(1H)-one hydrochlorideAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-ethyl-1-[4-(4-hydroxybenzoyl)-benzyl]-7-methylimidazo[1,2-a]pyrimidin-5(1H)-one (126 mg), 4-picolyl chloride hydrochloride (154 mg) and potassium carbonate (274 mg) in DMF (7 ml) was stirred at room temperature for 17 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform: methanol =19:1) and treated with hydrogen chloride/ethyl acetate to provide the title compound as colorless solid (140 mg).

Aufarbeitung

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform: methanol =19:1)
  7. additiontreated with hydrogen chloride/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ecd87a9660e14308a44c03ac8e584295
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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