Reacción #701559

Ecuación de reacción

6-dimethylamino-4-ethoxycarbonylpyrimidine

ethyl propionate

sodium hydride

→

ethyl 3-(6-dimethylaminopyrimidin-4-yl)-2-methyl-3-oxopropionate

Rendimiento 60.6%

Disolventes

1,2-dimethoxyethane

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture is refluxed
2. 2
   TemperaturaRefluxing
3. 3
   Temperaturais maintained for a further 30 minutes
4. 4
   OtroThe solvent is evaporated
5. 5
   OtroAfter decanting
6. 6
   Extracciónthe aqueous phase is again extracted with diethyl ether (450 cc)
7. 7
   LavadoThe combined organic phases are washed with an 8% (w/v) sodium bicarbonate solution (120 cc)
8. 8
   SecadoThey are dried over anhydrous magnesium sulphate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated to dryness under reduced pressure

Procedimiento

A solution of 6-dimethylamino-4-ethoxycarbonylpyrimidine (19.5 g) and ethyl propionate (11.2 g) in 1,2-dimethoxyethane (75 cc) is added to a suspension of sodium hydride (9.6 g) (50% in mineral oil) in 1,2-dimethoxyethane (25 cc), and the reaction mixture is refluxed. Refluxing is maintained for a further 30 minutes. The solvent is evaporated, and then the residue is taken up in diethyl ether (350 cc) and 4N hydrochloric acid (70 cc). After decanting, the aqueous phase is again extracted with diethyl ether (450 cc). The combined organic phases are washed with an 8% (w/v) sodium bicarbonate solution (120 cc). They are dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure to give ethyl 3-(6-dimethylaminopyrimidin-4-yl)-2-methyl-3-oxopropionate (15.2 g).

Fuente