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

HRID 1293033Notes

Reaction equation

HRID 1293033 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[C:7]1([CH:13]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:14][NH:15][C:16]2[N:24]=[C:23](SC)[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:39](=O)([O-])O.[Na+]>O.CC(C)=O>[C:33]1([CH:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][NH:15][C:16]2[N:24]=[C:23]([S:3]([CH3:39])(=[O:5])=[O:2])[N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 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-amineYield 75.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of Oxone (Trade Mark) (potassium peroxymonosulphate) (44 g, 71.7 mmol) in water (200 ml) was added dropwise over 2 hours to a solution of N-(2,2-diphenylethyl)-2-(methylsulfanyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (Preparation 21) (25 g, 56.2 mmol) and sodium hydrogencarbonate (20 g, 238 mmol) in a mixture of acetone (1000 ml) and water (250 ml). The resultant mixture was stirred at room temperature for 24 hours and filtered and the residue was washed with acetone. The acetone was removed from the filtrate under reduced pressure and the resulting aqueous residue was extracted with ethyl acetate and then dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residue was triturated with diethyl ether, filtered, washed with diethyl ether and pentane and then dried to afford the title compound as a white solid (20.32 g).

Workup

  1. filtrationfiltered
  2. washthe residue was washed with acetone
  3. customThe acetone was removed from the filtrate under reduced pressure
  4. extractionthe resulting aqueous residue was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was triturated with diethyl ether
  10. filtrationfiltered
  11. washwashed with diethyl ether and pentane
  12. customdried

Sources & evidence

ORD record
ord-3c8a4b5e881741138a81eb440f7a6301
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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