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Sodium hydride → 2-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-2,3-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochloride

HRID 1291325
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1291325
[K].[CH2:2]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[N:12][NH:13][C:7]=2[N:6]=[C:5]1[SH:14])[CH3:3].C[O-].[Na+].[ClH:18].[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][Cl:24].[H-].[Na+].[Cl:28][C:29]1[CH:44]=[CH:43][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=2)=[O:34])=[CH:31][CH:30]=1>CN(C=O)C>[ClH:24].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39][N:13]3[C:7]4[N:6]=[C:5]([S:14][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[N:4]([CH2:2][CH3:3])[C:9](=[O:10])[C:8]=4[CH:11]=[N:12]3)=[CH:37][CH:36]=2)=[O:34])=[CH:43][CH:44]=1.[ClH:18].[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:33]([C:35]2[CH:42]=[CH:41][C:38]([CH2:39][N:12]3[CH2:11][C:8]4[C:9](=[O:10])[N:4]([CH2:2][CH3:3])[C:5]([S:14][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])=[N:6][C:7]=4[NH:13]3)=[CH:37][CH:36]=2)=[O:34])=[CH:43][CH:44]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 10942334Sodium MethoxideHCID 178462982HCID 178462982, Verbindung

Produkt 2

HCID 18918829
2-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-2,3-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochloride
HCID 189192861-[4-(4-Chlorobenzoyl)benzyl]-6-(3-dimethylaminopropylthio)-5-ethyl-1,5-dihydro-4H-pyrazolo[3,4-d]-pyrimidin-4-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-ethyl-6-mercapto-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one potassium (2.0 g) in DMF (25 ml) was added 28% sodium methoxide (1.75 ml). Then, 3-dimethylaminopropyl chloride hydrochloride (1.62 g) was added and the mixture was stirred at 60° C. for 1 day. To this reaction mixture was added 60% sodium hydride (232 mg) and the mixture was stirred at room temperature for 10 minutes. Thereafter, 4-(4-chlorobenzoyl)benzyl bromide (1.778 g) was added and the reaction mixture was 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 (chloroform: methanol: concentrated aqueous ammonia=50:1:0.1) and treated with hydrogen chloride/ethyl acetate to provide the title compound (A) (518 mg) and (B) (262 mg) both as colorless solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. concentrationThis reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform: methanol: concentrated aqueous ammonia=50:1:0.1)
  9. additiontreated with hydrogen chloride/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c45b89f721d944f3b9771460643d568c
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05753664

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