Dimethylformamide → HCID 178503591, Verbindung

HRID 1736563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736563
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([O:14]C)=O)[C:8]([S:16][CH3:17])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[N:19]1[CH:24]=[CH:23][C:22]([C:25](N)=[NH:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=4)=[N:26][C:12](=[O:14])[C:9]3=[C:8]([S:16][CH3:17])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 2776844Pyridine-4-amidine hydrochloride2×HCID 12508124HCID 12508124, Verbindung

Produkt 1

HCID 178503591HCID 178503591, VerbindungAusbeute 12,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of methyl 1-cyclopentyl-3-methylthio-5-amino-1H-pyrazole-4-carboxylate (3.0 g, 0.012 mol), 4-pyridine carboxamidine hydrochloride (1.9 g, 0.012 mol), potassium carbonate (1.6 g, 0.012 mol) and DMF (25 ml) were refluxed for 4 hours. Additional 4-pyridinecarboxamidine hydrochloride (1.9 g) and potassium carbonate (1.6 g) were added and the reaction mixture was refluxed for 24 hours. The solution was poured into ice-water, neutralized with acetic acid and the resulting precipitate was collected by filtration and washed with water. Recrystallization of the solid from DMF afforded 0.48 g (12%) of 1-cyclopentyl-3-methylthio-6-(4-pyridyl )-pyrazolo [3,4-d]-pyrimidin-4-one as a white powder, m.p. 272°-274° C. when dried at 110° C. for 16 hours in high vacuum.

Aufarbeitung

  1. temperaturewere refluxed for 4 hours
  2. temperaturethe reaction mixture was refluxed for 24 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customRecrystallization of the solid from DMF

Quellen und Nachweise

ORD-Eintrag
ord-e346dee31e2c44bfbff1b74cb8ce2004
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541187

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