Reacción #420174

Ecuación de reacción

LiHMDS

4-methylpyrimidine

diethylcarbonate

→

title compound

Rendimiento 78.1%

ethyl 2-(pyrimidin-4-yl)acetate

Rendimiento 78.1%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction was slowly warmed to room temperature
2. 2
   workup.STIRRINGstirred for 4 days
3. 3
   OtroThe reaction mixture was quenched by addition of 1 N HCl
4. 4
   Extracciónextracted with EtOAc (3×)
5. 5
   SecadoThe combined organics were dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   Otropurified by flash chromatography on silica gel (0-100% EtOAc in hexanes)

Procedimiento

To a flask containing LiHMDS (32 mL, 31.89 mmol, 1.0 M in THF) at −70° C., was slowly added 4-methylpyrimidine (1.0 g, 10.63 mmol). After 5 min of stirring at −70° C., diethylcarbonate (1.93 mL, 15.95 mmol) was added, the reaction was slowly warmed to room temperature and stirred for 4 days. The reaction mixture was quenched by addition of 1 N HCl, neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (0-100% EtOAc in hexanes) to give the title compound as a yellow oil (1.38 g, 78%). MS 167 (MH+).

Fuente