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

HRID 1557

반응식

HRID 1557 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-560dc193ecc34b789acc357ab3f450a5
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726174

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