Acetone → 4-[(2-Amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol

HRID 241070Notes

Reaction equation

HRID 241070 reaction equation
[NH2:1][C:2]1[C:7]([S:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])=[CH:6][C:5]([Br:15])=[CH:4][N:3]=1.CC(C)=[O:18].O.S([O-])(O[O-])(=O)=O.[K+].[K+]>CO>[NH2:1][C:2]1[C:7]([S:8]([CH2:9][CH2:10][C:11]([CH3:12])([OH:13])[CH3:14])=[O:18])=[CH:6][C:5]([Br:15])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 10313463Potassium peroxymonosulphateHCID 66820470HCID 66820470, compound

Product 1

HCID 668205914-[(2-Amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-olYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[(2-amino-5-bromopyridin-3-yl)thio]-2-methylbutan-2-ol (83 mg, 0.28 mmol) in a mixture of methanol (750 μL), acetone (750 μL) and water (450 μL) was added potassium peroxymonosulfate (131 mg, 0.21 mmol) and the reaction mixture was stirred for 90 minutes at 0° C. The reaction mixture was partitioned between water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with water (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (35% to 80% ethyl acetate in hexane) gave 4-[(2-amino-5-bromopyridin-3-yl)sulfinyl]-2-methylbutan-2-ol (52 mg, 60%); MS (EI) for C10H15BrN2O2S: 308 (MH+).

Workup

  1. customThe reaction mixture was partitioned between water (20 mL) and ethyl acetate (50 mL)
  2. customThe organic layer was separated
  3. washwashed with water (20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (35% to 80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-562c0c0b70344e33823acd6ef6af8784
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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