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

HRID 335094Notes

Reaction equation

HRID 335094 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-88db2f685e0a4092a3e697ff7f17186f
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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