Sodium → 1-cyclopentyl-3-ethyl-6-imidazo[1,2-a]pyridin-6-yl-2H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 487268

Reaktionsgleichung

Reaktionsgleichung von HRID 487268
[Na].[C:2]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[CH:14][N:15]=2)[CH:12]=1)(OCC)=O.[CH:16]1([N:21]2[C:25]([NH2:26])=[C:24]([C:27]([NH2:29])=[O:28])[C:23]([CH2:30][CH3:31])=[N:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[CH:16]1([N:21]2[C:25]3=[N:26][C:2]([C:7]4[CH:8]=[CH:9][C:10]5[N:11]([CH:13]=[CH:14][N:15]=5)[CH:12]=4)=[N:29][C:27](=[O:28])[C:24]3=[C:23]([CH2:30][CH3:31])[NH:22]2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Komponenten

5

Edukt 3

HCID 5360545SodiumHCID 11830209Ethyl imidazo[1,2-a]pyridine-6-carboxylateHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Produkt 1

HCID 1784378341-cyclopentyl-3-ethyl-6-imidazo[1,2-a]pyridin-6-yl-2H-pyrazolo[3,4-d]pyrimidin-4-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium metal (0.21 g, 9.2 mmol) was dissolved in ethanol (25 ml) and 6-carboethoxyimidazo[1,2-a]pyridine (1.75 g, 9.2 mmol) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.02 g, 4.6 mmol) were added. The reaction mixture was heated to reflux for 24 hours, cooled to room temperature and stirred for 60 hours. The solvent was removed in vacuo, the residue was dissolved in water (100 ml) and the solution was neutralized by the addition of concentrated HCl. A precipitate was obtained which was collected by filtration through a glass frit. The solid was recrystallized from ethanol and washed with ether to afford 0.98 g (62%) of 1-cyclopentyl-3-ethyl-6-(6-imidazo[1,2-a]pyridinyl)-pyrazolo[3,4-d]pyrimidin-4-one as white crystals, m.p. >300° C. when dried for 18 hours at 120° C. in high vacuum.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in water (100 ml)
  5. additionthe solution was neutralized by the addition of concentrated HCl
  6. customA precipitate was obtained which
  7. filtrationwas collected by filtration through a glass frit
  8. customThe solid was recrystallized from ethanol
  9. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-19b4b463815840d1850298edd2de8c12
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294612

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