m-Chloroperbenzoic acid → 4-(4-Bromo-phenyl)-2-methanesulfinyl-pyrimidine

HRID 1434983Notes

Reaction equation

HRID 1434983 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14]([CH3:15])=[O:24])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 579362944-(4-Bromophenyl)-2-(methylthio)pyrimidine

Product 1

HCID 579361754-(4-Bromo-phenyl)-2-methanesulfinyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(4-Bromo-phenyl)-2-methylsulfanyl-pyrimidine (1.1 g, 3.91 mmol) in DCM (33 ml) was cooled to 0° C. and treated within 1 hour with several portions of mCPBA (content 70%, 1.1 g, 4.46 mmol) under TLC-control. 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 by chromatography on silicagel (acetone/hexanes:50/50 to 75/25) to give the title compound as white crystals. Yield: 700 mg (60%).

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 by chromatography on silicagel (acetone/hexanes:50/50 to 75/25)

Sources & evidence

ORD record
ord-392992da28bd449aa3e563a33df5512b
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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