Reacción #73209

Ecuación de reacción

DBU

4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine

ACN

senecionitrile

→

desired product

3-Methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to room temperature
2. 2
   Otrothe ACN was evaporated
3. 3
   workup.ADDITIONThe mixture was diluted with ethyl acetate
4. 4
   Lavadowashed with dilute HCl and brine
5. 5
   SecadoThe organic solution was dried over sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroPurification by silica gel chromatography (ethyl acetate/hexanes)

Procedimiento

To a solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (0.216 g, 0.684 mmol) in ACN (4 mL, 0.08 mol) was added crude senecionitrile (0.111 g, 1.37 mmol), followed by DBU (200 μL, 0.002 mol) and the resulting mixture was heated to 60° C. for 23 hours. The mixture was cooled to room temperature and the ACN was evaporated. The mixture was diluted with ethyl acetate and washed with dilute HCl and brine. The organic solution was dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (ethyl acetate/hexanes) afforded the desired product.

Fuente