Water → HCID 18362948, compound

HRID 1976834Notes

Reaction equation

HRID 1976834 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]1[C:18]([S:19]([CH2:21][CH2:22][CH2:23][OH:24])=[O:20])=[C:17]2[C:12]([N:13]([CH:28]([CH3:30])[CH3:29])[C:14](=[O:27])[N:15]([CH3:26])[C:16]2=[O:25])=[CH:11]1.ClC1C=C(C=CC=1)C(OO)=[O:36].O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]1[C:18]([S:19]([CH2:21][CH2:22][CH2:23][OH:24])(=[O:36])=[O:20])=[C:17]2[C:12]([N:13]([CH:28]([CH3:30])[CH3:29])[C:14](=[O:27])[N:15]([CH3:26])[C:16]2=[O:25])=[CH:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 18362925HCID 18362925, compound2×

Product 1

HCID 18362948HCID 18362948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 8, 6-(2,3-Dihydro-1H-inden-2-yl)-5-[(3-hydroxypropyl)sulphinyl]-3-methyl-1-(1-methylethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (80 mg), was dissolved in dichloromethane (5 ml) and 3-chloroperoxybenzoic acid (57-85%) (50 mg) was added. The reaction mixture was stirred for 75 minutes then water and sodium metabisulphite (45 mg) were added and the mixture was stirred for 5 minutes. The phases were separated and the organic phase was washed with sodium bicarbonate (aqueous), then dried, filtered and evaporated. The resultant foam was recrystallised from isohexane-ethyl acetate-ether to give the title compound (15 mg).

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. customThe phases were separated
  3. washthe organic phase was washed with sodium bicarbonate (aqueous)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant foam was recrystallised from isohexane-ethyl acetate-ether

Sources & evidence

ORD record
ord-4d1998423b974b5c8df70458b65d2b62
Source dataset
uspto-grants-2001_05
Patent number
US06229013B1

Reaction notes

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