Triethylamine → 8-(6-Chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane

HRID 75447

Reaktionsgleichung

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:3]=1.Cl.[CH:19]12[NH:26][CH:23]([CH2:24][CH2:25]1)[CH2:22][O:21][CH2:20]2.C(N(CC)CC)C>ClCCl>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:3]=[C:2]([N:26]2[CH:19]3[CH2:25][CH2:24][CH:23]2[CH2:22][O:21][CH2:20]3)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

In a 250 mL round-bottomed flask was placed 4,6-dichloro-2-(4-nitrophenyl)pyrimidine (59, 192 mg, 0.711 mmol) in dichloromethane (8 mL) to give a colorless solution. 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (33, 106 mg, 0.711 mmol) was added and the solution was cooled to 0° C. Triethylamine (0.297 mL, 2.133 mmol) was added slowly and the mixture was allowed to slowly warm to room temperature, and stirred for 16 hours at room temperature. The mixture was heated under reflux for 2 hours, diluted with dichloromethane and washed with saturated NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated. the crude product was applied to a silica gel column and eluted with 5-40% EtOAc in hexanes to give the title compound (212 mg, 86%). The sample was identical to the same compound prepared according to Scheme 16. HRMS: For [M+H]+ mass error=0.1 mDa or 0.39 ppm.

Aufarbeitung

customIn a 250 mL round-bottomed flask was placed
temperatureto slowly warm to room temperature
temperatureThe mixture was heated
temperatureunder reflux for 2 hours
washwashed with saturated NaHCO3
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
washeluted with 5-40% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag: ord-9601be6a4117446e90a01707e9dd8e4e
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835429B2

Verknüpfte Notizen

Wird geladen…