Reacción #1650

Ecuación de reacción

sodium hydride

chloromethoxy(diethylphosphonomethoxy)methane

cytosine

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]cytosine

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe volatiles were removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (120 mL)
3. 3
   LavadoThe organic phase was washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   OtroAfter removal of the solvent in vacuo
6. 6
   Otrothe residual oil was chromatographed on silica gel

Procedimiento

To a suspension of 60% sodium hydride in mineral oil (700 mg, 17 mmol) in DMF (50 mL) was added cytosine (1.9 g, 17 mmol) and the mixture was heated at 80° C. for 2 hr under nitrogen. To the resulting yellow solution was added dropwise a solution of chloromethoxy(diethylphosphonomethoxy)methane [prepared from diethylphosphate (2.4 g, 17 mmol) and bis-(chloromethoxy)methane (12.5 g, 86 mmol)] in DMF (10 mL) under nitrogen. After stirring 15 hr at 25° C., the volatiles were removed in vacuo. The residue was dissolved in ethyl acetate (120 mL) and water (30 mL). The organic phase was washed with brine and dried (MgSO4). After removal of the solvent in vacuo, the residual oil was chromatographed on silica gel using CH2Cl2 /10% MeOH as eluent to give the title compound as a white oil: yield 1.2 g (22%).

Fuente