Hydrogen Peroxide → 5-Bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

HRID 1504759Notes

Reaction equation

HRID 1504759 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH-:19].[Na+].OO>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[N:12]=2)[C:5]([C:8]([NH2:9])=[O:19])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 867316505-Bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

Product 1

HCID 867316575-Bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (PrepEx 1.4) (2.6 g, 8.6 mmol) in DMSO (60 mL) was added sodium hydroxide (6.0 M in water, 1.4 mL, 8.6 mmol). The reaction mixture was cooled in an ice bath, and hydrogen peroxide (30% w/w solution in water, 2.0 mL, 20 mmol) was added. After 2 hours, the reaction mixture was diluted with water (100 mL) and stirred. After 10 min, the reaction mixture was filtered, and the collected solids were washed with water (2×50 mL) and dried under reduced pressure to afford 5-bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide. 1H NMR (600 MHz, CD3OD) δ 9.63 (d, J=2.4 Hz, 1H), 8.07 (d, J=2.4 Hz, 1H), 6.63 (s, 1H), 6.48 (s, 1H), 2.40 (s, 3H), 2.24 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. waitAfter 10 min
  3. filtrationthe reaction mixture was filtered
  4. washthe collected solids were washed with water (2×50 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-110228e14dc1492fb30ab223891a99a6
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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