Methyl iodide → N-(5-methoxy-3-phenoxypyridin-2-yl)-4-methylthiazol-2-amine

HRID 911782Notes

Reaction equation

HRID 911782 reaction equation
IC.[CH3:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:7][CH:8]=1.[C:24](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][O:16][C:13]1[CH:12]=[C:11]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH3:3])[N:5]=2)=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 247645186-(4-Methylthiazol-2-ylamino)-5-phenoxypyridin-3-ol

Product 1

HCID 57742647N-(5-methoxy-3-phenoxypyridin-2-yl)-4-methylthiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.0362 g, 0.255 mmol) is added to a mixture of 6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ol (0.255 mmol) and potassium carbonate (0.0794 g, 0.574 mmol) in DMF (3 mL) and stirred overnight at room temperature. The reaction mixture is partitioned between water and ether. The organic layer is washed with water, dried, and concentrated. The residue is purified by silica gel chromatography, eluting with 15-20% EtOAc in hexanes, to afford the title compound.

Workup

  1. customThe reaction mixture is partitioned between water and ether
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with 15-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-cb5951528104445c9c54786cd18d487e
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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