m-Chloroperbenzoic acid → 2-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348435Notes

Reaction equation

HRID 348435 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1>ClCCl.ClCCl.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17]([CH3:18])=[O:27])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58802987N-(4-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxamide

Product 1

HCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amideYield 73.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a solution of 2-methylsulfanylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (2.00 g, 7.60 mmol) in dichloromethane (76 mL) was added m-CPBA (67%, 2.02 g, 7.84 mmol) in one portion. Solid precipitate appeared within 2 min, and after 10 min the solution was diluted with 2/1 dichloromethane/hexane (60 mL). The solids were collected by filtration and washed with 50% dichloromethane/hexane to afford, after drying, 1.558 g (73% yield) of the titled sulfoxide. A second crop was obtained by concentrating the filtrate and triturating the solids first with hot 2/1 dichloromethane/hexane, and then after filtration by a second trituration with acetone. An additional 0.22 g (10%) of titled product was obtained, and was shown by 1H NMR to be contaminated with 10% sulfone.

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with 50% dichloromethane/hexane
  3. customto afford
  4. customafter drying

Sources & evidence

ORD record
ord-df9c7ac5308a49a8aff0716f4f50424b
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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