Sodium hydride → 5-Ethyl-2-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1291326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1291326
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[CH:10]=[N:11][NH:12][C:6]=2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2].[H-].[Na+].[CH3:17][O:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>CN(C=O)C>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2[CH:10]=[N:11][N:12]([CH2:29][C:28]3[CH:27]=[CH:26][C:25]([C:23](=[O:24])[C:22]4[CH:33]=[CH:34][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[CH:32][CH:31]=3)[C:6]=2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2].[CH2:1]([N:3]1[C:8](=[O:9])[C:7]2=[CH:10][N:11]([CH2:29][C:28]3[CH:27]=[CH:26][C:25]([C:23](=[O:24])[C:22]4[CH:33]=[CH:34][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[CH:32][CH:31]=3)[N:12]=[C:6]2[N:5]=[C:4]1[S:13][CH3:14])[CH3:2]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 131506704-(4-Methoxybenzoyl)benzyl bromideHCID 189190765-ethyl-6-methylthio-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

Produkt 2

HCID 189188625-Ethyl-2-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-oneHCID 189189835-Ethyl-1-[4-(4-methoxybenzoyl)benzyl]-6-methylthio-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-ethyl-6-methylthio-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (900 mg) in DMF (20 ml) was added 60% sodium hydride (207 mg) and the mixture was stirred at room temperature for 10 minutes. Then, 4-(4-methoxybenzoyl)benzyl bromide (1.31 g) was added and the mixture was further stirred at room temperature for 30 minutes. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate-chloroform=3:2:1) to provide the title compounds (A) (400 mg) and (B) (366 mg) both as white solid.

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 30 minutes
  2. concentrationThis reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate-chloroform=3:2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f2021d725b27474aaf83e2c532a583fa
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753664

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