Hexane → (4-Amino-2-(ethylsulfinyl)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

HRID 1371668Notes

Reaction equation

HRID 1371668 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([S:20][CH2:21][CH3:22])[N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:28].CCCCCC>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([F:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4]([S:20]([CH2:21][CH3:22])=[O:28])[N:3]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 70297m-Chloroperbenzoic acidHCID 11723824(4-Amino-2-(ethylthio)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

Product 1

HCID 21070554(4-Amino-2-(ethylsulfinyl)pyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-(2,3-difluoro-6-methoxy-phenyl)-methanone (7.4 g, 23 mmol, Example 102) in dichloromethane (150 mL) at 0° C. was treated portionwise with 74% meta-chloroperoxybenzoic acid (6 g, 26 mmol) over about 30 minutes. The cold reaction mixture was quenched with 25 ml of 10% aqueous sodium thiosulfate solution and the layers separated. The organic layer was washed once with 10% aqueous sodium thiosulfate solution, twice with saturated aqueous sodium carbonate solution, once with brine, dried (Na2SO4) and evaporated. Trituration of the residue with hexane provided a quantitative yield of (4-amino-2-ethanesulfinyl-pyrimidin-5-yl)-(2,3-difluoro-6-methoxy-phenyl)-methanone as a colorless solid, mp 165 dec. Mass Spectrum (LR-ES) (M+H)+: 342.

Workup

  1. customThe cold reaction mixture
  2. customwas quenched with 25 ml of 10% aqueous sodium thiosulfate solution
  3. customthe layers separated
  4. washThe organic layer was washed once with 10% aqueous sodium thiosulfate solution, twice with saturated aqueous sodium carbonate solution, once with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4d332b800e0f43dab6d61e6624508941
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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