Methyl iodide → 5-Bromo-1,4-dimethyl-1,2-dihydropyridin-2-one

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-bromo-4-methylpyridin-2(1H)-one (164 mg, 0.872 mmol) and iodomethane (124 mg, 0.872 mmol) in DMSO (3 mL) was added potassium carbonate (121 mg, 0.872 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

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

Sources & evidence

ORD record: ord-fe8fd08f64a148a9b12e5008fd63ca04
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Reaction notes

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Participants

Reactant 3

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 8199375-Bromo-2-hydroxy-4-methylpyridine

Product 1

HCID 672818265-Bromo-1,4-dimethyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent