Sodium Thiosulfate → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidine

HRID 32523Notes

Reaction equation

HRID 32523 reaction equation
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][N:13]1[C:17]([C:18]2[S:28][C:21]3[N:22]=[CH:23][N:24]=[C:25](SC)[C:20]=3[CH:19]=2)=[C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]=[CH:14]1.[O-:35][S:36]([O-:39])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:12][N:13]1[C:17]([C:18]2[S:28][C:21]3[N:22]=[CH:23][N:24]=[C:25]([S:36]([CH3:1])(=[O:39])=[O:35])[C:20]=3[CH:19]=2)=[C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 99278256-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine

Product 1

HCID 179657746-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylsulfonyl)thieno[2,3-d]pyrimidineYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (70-75%, 105 mg) was added to a stirred solution of 6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine (example 7) (72 mg) in DCM (5 mL), stirred for 6 hours then 2M Na2S2O3 (2.5 mL) was added. The organic layer was separated and the aqueous layer extracted with DCM (2×15 mL). The combined organics were washed with saturated aqueous NaHCO3 (10 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:4) afforded the title compound as a yellow solid (44 mg, 56%);

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with DCM (2×15 mL)
  3. washThe combined organics were washed with saturated aqueous NaHCO3 (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica eluting with hexane:EtOAc (1:4)

Sources & evidence

ORD record
ord-cc4330b7819b447695cc0f3603161c48
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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