Reaction #1653

Reaction equation

diisopropylethylamine

2-acetamido-6-diphenylcarbamoyl-9-[2-(phenylselenyl)ethoxymethyl]purine

H2O2

sodium bicarbonate

→

title compound

2-Acetamido-6-diphenylcarbamoyl-9-(vinyloxymethyl)purine

Solvents

dioxane

Conditions

Workup

1. 1
   ConcentrationThe reaction was then concentrated to about 10 mL
2. 2
   workup.ADDITIONdiluted with ethyl acetate (100 mL)
3. 3
   Dryingdried (MgSO4)
4. 4
   Otherthe solvents were removed in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in dioxane (40 mL)
6. 6
   Temperaturethe solution was heated at 80° C. for 30 min under nitrogen
7. 7
   OtherThe solvent was evaporated in vacuo
8. 8
   Otherthe residual oil was chromatographed on silica gel

Procedure

To a solution of 2-acetamido-6-diphenylcarbamoyl-9-[2-(phenylselenyl)ethoxymethyl]purine (4.92 g, 8.16 mmol) in dioxane (80 mL) was added 30% H2O2 (4 mL, 35 mmol) and sodium bicarbonate (2.1 g, 24.5 mmol). The mixture was heated at 60° C. for 20 min. The reaction was then concentrated to about 10 mL, diluted with ethyl acetate (100 mL), dried (MgSO4) and the solvents were removed in vacuo. The residue was dissolved in dioxane (40 mL), diisopropylethylamine (1.27 g, 10 mmol) was added and the solution was heated at 80° C. for 30 min under nitrogen. The solvent was evaporated in vacuo and the residual oil was chromatographed on silica gel using CH2Cl2 -ethyl acetate (1:1) as eluent to give the title compound as a yellowish powder: yield 2.3 g (65%).

Source