Triethylamine → 3-(1-isopropyl-6-(4-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1093186Notes

Reaction equation

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]

Participants

Conditions

Temperature: 140 °C

Procedure

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)+

Workup

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

Sources & evidence

ORD record: ord-f47737fbb8174cb0ad7fcfb9bce70d42
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129371B2

Reaction notes

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