Reacción #162629

Ecuación de reacción

4,6-dichloro-2-(4-nitrophenyl)pyrimidine

4,6-Dichloro-2-(4-nitrophenyl)pyrimidine

3-oxa-8-azabicyclo[3.2.1]octane hydrochloride

Triethylamine

→

title compound

Rendimiento 86.0%

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

Rendimiento 86.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 250 mL round-bottomed flask was placed
2. 2
   Temperaturato slowly warm to room temperature
3. 3
   TemperaturaThe mixture was heated
4. 4
   Temperaturaunder reflux for 2 hours
5. 5
   Lavadowashed with saturated NaHCO3
6. 6
   SecadoThe organic phase was dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   Lavadoeluted with 5-40% EtOAc in hexanes

Procedimiento

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.

Fuente