Methanol → HCID 58541669, compound

HRID 600254Notes

Reaction equation

HRID 600254 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](SC)[N:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.O[O:25][S:26]([O-:28])=O.[K+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[CH3:42]O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([S:26]([CH3:42])(=[O:28])=[O:25])[N:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24412Potassium PersulfateHCID 23707502Potassium hydroxy sulfiteHCID 58541652HCID 58541652, compound

Product 1

HCID 58541669HCID 58541669, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-(4-fluorophenyl)-5-[2-(methylsulfanyl)pyrimidin-4-yl]imidazo[2,1-b][1,3]oxazole (E) (2.0 g, 6.13 mmol) in methanol (250 mL) is slowly added Oxone™ (potassium monopersulfate) (11.3 g, 18.4 mmol) in water (50 mL). The mixture is stirred at room temperature for 24 hours. The solvent is removed in vacuo and the residue dissolved in dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The solids are removed by filtration and the solvent removed in vacuo. The residue is purified by silica gel column chromatography to provide 6-(4-fluorophenyl)-5-[2-(methylsulfonyl)pyrimidin-4-yl]imidazo[2,1-b][1,3]oxazole (F) (Compound XI, Table 1)) as a white solid (1.8 g, 82%).

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solids are removed by filtration
  6. customthe solvent removed in vacuo
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3510c02de09c41d68e482869215ca6ec
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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