Sodium Sulfite → Tert-butyl 2-(methylsulfonyl)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

HRID 546439Notes

Reaction equation

HRID 546439 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[C:12]([O:16][C:17]([N:19]1[CH2:27][C:26]2[CH:25]=[N:24][C:23](SC)=[N:22][C:21]=2[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[S:30]([O-:33])([O-])=[O:31].[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:27][C:26]2[CH:25]=[N:24][C:23]([S:30]([CH3:2])(=[O:33])=[O:31])=[N:22][C:21]=2[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18442822Tert-butyl 2-(methylthio)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

Product 1

HCID 18442821Tert-butyl 2-(methylsulfonyl)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (1.99 g) was added to a dichloromethane solution (20 ml) of 6-(tert-butoxy-carbonyl)-5,7-dihydro-2-methylthiopyrrolo[3,4-d]-pyrimidine (1.08 g) under ice cooling, and the mixture was stirred for 5 hours. A saturated aqueous solution of sodium sulfite, a saturated aqueous solution of sodium hydrogen carbonate and dichloromethane were added to separate an organic layer. The organic layer was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, hexane was added to the residue, and powder deposited was collected by filtration to obtain the title compound (1.09 g) as colorless powder.

Workup

  1. customto separate an organic layer
  2. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure, hexane
  4. additionwas added to the residue, and powder
  5. filtrationdeposited was collected by filtration

Sources & evidence

ORD record
ord-28ee22c8276b41038e9c2c083a1e5682
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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