Sodium Bicarbonate → N-(2,2-Diphenylethyl)-2-(methylsulphonyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 2268406Notes

Reaction equation

HRID 2268406 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[C:15]1([CH:21]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:22][NH:23][C:24]2[N:32]=[C:31](SC)[N:30]=[C:29]3[C:25]=2[N:26]=[CH:27][N:28]3[CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:47](=O)([O-])O.[Na+]>O.CC(C)=O>[C:41]1([CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22][NH:23][C:24]2[N:32]=[C:31]([S:3]([CH3:47])(=[O:5])=[O:2])[N:30]=[C:29]3[C:25]=2[N:26]=[CH:27][N:28]3[CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 21978277N-(2,2-diphenylethyl)-2-(methylsulphanyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21978255N-(2,2-Diphenylethyl)-2-(methylsulphonyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of oxone® (potassium peroxymonosulphate) (44 g, 71.7 mmol) in water (200 ml) was added drop wise over 2 hr to a stirred solution of N-(2,2-diphenylethyl)-2-(methylsulfanyl)-9-tetrahydro-2Hpyran-2-yl-9H-purin-6-amine (preparation 7) (25 g, 56.2 mmol) and sodium hydrogen carbonate (20 g, 238 mmol) in acetone (1000 ml) and water (250 ml). The resultant mixture was stirred at room temperature for 24 hr, filtered and the residue washed with acetone. The acetone was removed from the filtrate under reduced pressure and the resulting aqueous residue extracted with ethyl acetate and then dichloromethane. The combined organic extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was triturated with diethyl ether, the mixture filtered and the collected material washed with diethyl ether and pentane, then dried to afford the title compound as a white solid (20.32 g).

Workup

  1. filtrationfiltered
  2. washthe residue washed with acetone
  3. customThe acetone was removed from the filtrate under reduced pressure
  4. extractionthe resulting aqueous residue extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was triturated with diethyl ether
  10. filtrationthe mixture filtered
  11. washthe collected material washed with diethyl ether and pentane
  12. customdried

Sources & evidence

ORD record
ord-115eb3b9c4184aa1924789440ae766d4
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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