Hydrogen Peroxide → 2-Acetamido-6-diphenylcarbamoyl-9-(vinyloxymethyl)purine

HRID 1938797Notes

Reaction equation

HRID 1938797 reaction equation
[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[CH2:14][O:15][CH2:16][CH2:17][Se]C2C=CC=CC=2)=[C:7]([C:25](=[O:39])[N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:6]=1)(=[O:3])[CH3:2].OO.C(=O)(O)[O-].[Na+].C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:1]([NH:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[CH2:14][O:15][CH:16]=[CH2:17])=[C:7]([C:25](=[O:39])[N:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 189393722-Acetamido-6-diphenylcarbamoyl-9-[2-(phenylselenyl)ethoxymethyl]purine

Product 1

HCID 189394202-Acetamido-6-diphenylcarbamoyl-9-(vinyloxymethyl)purine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

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%).

Workup

  1. concentrationThe reaction was then concentrated to about 10 mL
  2. additiondiluted with ethyl acetate (100 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed in vacuo
  5. dissolutionThe residue was dissolved in dioxane (40 mL)
  6. temperaturethe solution was heated at 80° C. for 30 min under nitrogen
  7. customThe solvent was evaporated in vacuo
  8. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-27a6f5214d0d4108854fc56717471fe0
Source dataset
uspto-grants-1997_12
Patent number
US05693798

Reaction notes

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