m-Chloroperbenzoic acid → 6-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine

HRID 1453673Notes

Reaction equation

HRID 1453673 reaction equation
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[I:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]=[CH:21][N:22]([CH3:35])[C:23]=2[C:24]2[S:34][C:27]3[N:28]=[CH:29][N:30]=[C:31](SC)[C:26]=3[CH:25]=2)[CH:16]=[CH:17][CH:18]=1.[S:36](S([O-])=O)([O-:39])(=O)=[O:37].[Na+].[Na+]>C(Cl)Cl>[I:12][C:13]1[CH:14]=[C:15]([C:19]2[N:20]=[CH:21][N:22]([CH3:35])[C:23]=2[C:24]2[S:34][C:27]3[N:28]=[CH:29][N:30]=[C:31]([S:36]([CH3:1])(=[O:39])=[O:37])[C:26]=3[CH:25]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 690545946-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine

Product 1

HCID 690581946-(4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (70-75%, 399 mg) was added to a solution of 6-[4-(3-iodophenyl)-1-methyl-1H-imidazol-5-yl]-4-(methylthio)thieno[2,3-d]pyrimidine (300 mg) in DCM (20 mL) and stirred for 24 hours. Aqueous sodium metabisulfite was added and the mixture extracted with DCM. The organic phase was washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a yellow solid (220 mg, 68%);

Workup

  1. extractionthe mixture extracted with DCM
  2. washThe organic phase was washed with saturated aqueous NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72d403044d364d35b636923ddd5e4d92
Source dataset
uspto-grants-2009_01
Patent number
US07476677B2

Reaction notes

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