Methyl iodide → 5-Bromo-1,6-dimethyl-1H-pyridin-2-one

HRID 58051Notes

Reaction equation

HRID 58051 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].IC.[C:12]([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[N:6]([CH3:12])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27344173-Bromo-6-hydroxy-2-methylpyridine

Product 1

HCID 672819385-Bromo-1,6-dimethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-6-methylpyridin-2(1H)-one (164 mg, 0.872 mmol) and iodomethane (0.065 mL, 1.047 mmol) in DMSO (3 mL) was added K2CO3 (145 mg, 1.047 mmol). The mixture was stirred at 60° C. overnight, filtered, and purified via preparative HPLC, eluting with a gradient of 20-70% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) to give the title compound.

Workup

  1. filtrationfiltered
  2. custompurified via preparative HPLC
  3. washeluting with a gradient of 20-70% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-dd0bac2e0d6f483b8c081e4f44f0112d
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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