反应 #1650

反应方程式

sodium hydride

chloromethoxy(diethylphosphonomethoxy)methane

cytosine

→

title compound

1-[(Diethylphosphonomethoxy)methoxymethyl]cytosine

溶剂

DMF

DMF

反应条件

后处理

1. 1
   其他the volatiles were removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (120 mL)
3. 3
   洗涤The organic phase was washed with brine
4. 4
   干燥dried (MgSO4)
5. 5
   其他After removal of the solvent in vacuo
6. 6
   其他the residual oil was chromatographed on silica gel

实验过程

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%).

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