Triethylamine → 3-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane
Reaktionsgleichung
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:17]([CH:20]([CH3:22])[CH3:21])[N:18]=[CH:19][C:3]=12.Cl.[CH:24]12[O:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][NH:26][CH2:25]2.C(N(CC)CC)C>C(O)C>[CH:20]([N:17]1[C:4]2=[N:5][C:6]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[N:7][C:2]([N:26]3[CH2:25][CH:24]4[O:31][CH:28]([CH2:29][CH2:30]4)[CH2:27]3)=[C:3]2[CH:19]=[N:18]1)([CH3:22])[CH3:21]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
A suspension of crude 4-chloro-1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (2.5 mmol maximum) and 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride (0.47 g, 3.1 mmol) in ethanol (12 mL) was treated with triethylamine (1.1 mL) and then heated for 20 minutes in the microwave reactor at 140° C. At the completion of the reaction, the mixture was refrigerated overnight before collection of the precipitate via Buchner filtration. The solid was washed with methanol and dried under house vacuum to provide 3-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane as a yellow powder (0.96 g, 97% over 2 steps). MS (ES+): 394.9, 396.0 (M+H)+
Aufarbeitung
- customAt the completion of the reaction
- filtrationthe mixture was refrigerated overnight before collection of the precipitate via Buchner filtration
- washThe solid was washed with methanol
- customdried under house vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-f47737fbb8174cb0ad7fcfb9bce70d42
- Quelldatensatz
- uspto-grants-2012_03
- Patentnummer
- US08129371B2
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