Potassium Carbonate → 6,7-Dihydro-1,6,7-trimethylpyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4(1H)-one

HRID 260519

Reaktionsgleichung

Reaktionsgleichung von HRID 260519
[SH:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[CH:10]=[N:9][N:8]([CH3:11])[C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH:22](Br)[CH3:23])[CH3:21]>CN(C)C=O>[CH3:11][N:8]1[C:6]2[N:7]=[C:2]3[S:1][CH:22]([CH3:23])[CH:20]([CH3:21])[N:3]3[C:4](=[O:12])[C:5]=2[CH:10]=[N:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 215082,3-DibromobutaneHCID 178481768HCID 178481768, Verbindung

Produkt 1

HCID 224016736,7-Dihydro-1,6,7-trimethylpyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4(1H)-oneAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In 200 ml of dimethylformamide was dissolved 10.0 g (54.9 mmol) of 4,5-dihydro-6-mercapto-1-methylpyrazolo[3,4-d]pyrimidin-4(1H)-one [Helv. Chim. Acta, 42, 349 (1959)], and 15.2 g (110 mmol) of potassium carbonate and 10.1 ml (82.3 mmol) of 2,3-dibromobutane were added to the solution, followed by stirring at 80° C. for 3 hours. After evaporation of the solvent, the residue was subjected to partition between chloroform and water, and the chloroform layer was concentrated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform to give 1.57 g (12%) of Compound 41. The compound was recrystallized from ethyl acetate/hexane for purification.

Aufarbeitung

  1. additionwere added to the solution
  2. customAfter evaporation of the solvent
  3. customto partition between chloroform and water
  4. concentrationthe chloroform layer was concentrated to dryness under reduced pressure
  5. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2f37cf315c344f1a8a4df1cb3158c984
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527908

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