Methyl iodide → HCID 67417671, compound

HRID 625968Notes

Reaction equation

HRID 625968 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[NH:11][C:12]([I:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CO>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[N:11]([CH3:17])[C:12]([I:15])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67418588HCID 67418588, compound

Product 1

HCID 67417671HCID 67417671, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(benzyloxy)-6-iodopyridin-2(1H)-one (20.48 g, 62.6 mmol) in methanol (626 mL) was added potassium carbonate (8.56 g, 62.6 mmol) and iodomethane (3.91 mL, 62.6 mmol), and the resulting mixture was stirred at room temperature for 2 days. The mixture was concentrated under reduced pressure, and the resulting residue was partitioned between water and ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate, and purified using silica gel chromatography to afford 3-(benzyloxy)-6-iodo-1-methylpyridin-2(1H)-one (15.4 g, 45.1 mmol, 72% yield). ES-MS (M+H)+=342.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was removed
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. custompurified

Sources & evidence

ORD record
ord-383ae8e4be594463a7d279ced702fc61
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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