m-Chloroperbenzoic acid → 4-(5-Bromo-thiophen-2-yl)-2-methanesulfinyl-pyrimidine

HRID 1434919Notes

Reaction equation

HRID 1434919 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13]([CH3:14])=[O:23])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 28205344-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidine

Product 1

HCID 579361574-(5-Bromo-thiophen-2-yl)-2-methanesulfinyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-Bromo-thiophen-2-yl)-2-methylsulfanyl-pyrimidine (144 mg, 0.5 mmol) was dissolved in DCM (5 ml) and treated at 0° C. with mCPBA (content 70%, 112 mg, 0.65 mmol) for 15 minutes. The reaction mixture was washed with 2N-solution of sodium carbonate, the organic phase dried over sodium sulfate, filtered and evaporated to dryness and purified via chromatography on silicagel (acetone/hexanes:20/80 to 40/60) to give the title compound as white crystals. Yield: 120 mg (80%).

Workup

  1. washThe reaction mixture was washed with 2N-solution of sodium carbonate
  2. dry with materialthe organic phase dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified via chromatography on silicagel (acetone/hexanes:20/80 to 40/60)

Sources & evidence

ORD record
ord-15babf4ab00045bbb2715447b9d92996
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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