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

HRID 1806028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1806028
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d9587074e727471897b36c6064dfda84
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354540B2

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