Reacción #2104

Ecuación de reacción

diethyl phosphite

sodium hydride

1-(5-bromopentyl)-7-ethoxymethyl-3-methylxanthine

→

Diethyl [5-(7-ethoxymethyl-3-methylxanthin-1-yl)pentyl]phosphonate

Disolventes

dimethylformamide

dimethyl-formamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 4 hours at 20° C.
2. 2
   Otrothe reaction mixture was quenched with a little saturated ammonium chloride solution
3. 3
   Concentraciónconcentrated
4. 4
   Otrochromatographed on silica gel (eluent: dichloromethane/methanol 15:1)

Procedimiento

4.8 g (0.035 mol) of diethyl phosphite were cooled to 0° C. in 100 ml of dry dimethylformamide and slowly treated with 0.8 g (0.035 mol) of sodium hydride. The solution was stirred at 20° C. for 0.5 hours to complete the deprotonation and then treated with 10 g (0.0268 mol) of 1-(5-bromopentyl)-7-ethoxymethyl-3-methylxanthine, dissolved in a little dimethyl-formamide. After 4 hours at 20° C., the reaction mixture was quenched with a little saturated ammonium chloride solution, concentrated and chromatographed on silica gel (eluent: dichloromethane/methanol 15:1).

Fuente