Methyl iodide → HCID 90409027, compound

HRID 594044Notes

Reaction equation

HRID 594044 reaction equation
[Br:1][C:2]1[C:3]([OH:14])=[N:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH3:15])[CH:5]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178517833HCID 178517833, compound

Product 1

HCID 90409027HCID 90409027, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-morpholinopyridin-2-ol (1.0 equiv.) in DMF (0.1 M) was added potassium carbonate (2.0 equiv.) and iodomethane (1.0 equiv.). The solution was stirred at room temperature for 3 hours. Partitioned between water and ethyl acetate, the organic phase was washed with brine, dried with sodium sulfate, filtered and concentrated to dryness. Isolated 3-bromo-1-methyl-5-morpholinopyridin-2(1H)-one in 87% yield. LCMS (m/z) (M+H)=273.0/275.0, Rt=0.41 min.

Workup

  1. customPartitioned between water and ethyl acetate
  2. washthe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b0e4cd1323844193af708d9466b2c091
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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