Hydrogen Peroxide → [5-(4-Methanesulfinyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 908161Notes

Reaction equation

HRID 908161 reaction equation
[OH:1]O.[CH3:3][C:4]1[N:5]=[C:6]([NH:17][C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)(=O)C.O>[CH3:16][S:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]2[S:7][C:6]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)=[N:5][C:4]=2[CH3:3])=[CH:10][CH:11]=1)=[O:1]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86761401[4-Methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine

Product 1

HCID 85996777[5-(4-Methanesulfinyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amineYield 32.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Hydrogen peroxide solution (27% in water) (35 ml, 0.28 mmol) is added to a stirred suspension of [4-methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine (27c) (0.090 g, 0.28 mmol) in acetic acid (5 ml). After 30 minutes the reaction is diluted with water and brought to pH 10 by addition of aqueous sodium hydroxide. The product is extracted with ethyl acetate (3×50 ml), the combined organic extracts are washed with brine (50 ml), dried (MgSO4) and the solvent removed to give the title compound as an orange solid (0.03 g).

Workup

  1. extractionThe product is extracted with ethyl acetate (3×50 ml)
  2. washthe combined organic extracts are washed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed

Sources & evidence

ORD record
ord-0e7f6baab84e4525ac02068853f179b1
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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