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

HRID 1168281Notes

Reaction equation

HRID 1168281 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-(methylsulphanyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (Preparation 3) (25 g, 56.2 mmol) and sodium hydrogen carbonate (20 g, 238 mmol) in acetone (1000 ml) and water (250 ml). The resulting 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 (1000 ml) and then dichloromethane (1000 ml). The combined organic layers were washed with brine, dried (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 (1000 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (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-adf00bbf4fd4490288731bfe4512be16
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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