Cesium carbonate → 3-(6-Chloro-3-methylpyridazin-4-yloxy)pyridin-2-amine

HRID 1809644

Reaktionsgleichung

Reaktionsgleichung von HRID 1809644
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:10]1[CH:15]=[C:14]([Cl:16])[N:13]=[N:12][C:11]=1[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[Cl:16][C:14]1[N:13]=[N:12][C:11]([CH3:17])=[C:10]([O:8][C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 281142-Amino-3-HydroxypyridineHCID 587170494,6-Dichloro-3-methylpyridazine

Produkt 1

HCID 866411083-(6-Chloro-3-methylpyridazin-4-yloxy)pyridin-2-amineAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Aminopyridin-3-ol (5.0 g, 45.4 mmol) and 4,6-dichloro-3-methylpyridazine (7.4 g, 45.4 mmol, prepared according to WO 2003/041712) were dissolved in DMSO (100 mL). Cs2CO3 (16.3 g, 49.9 mmol) was added and the reaction stirred at ambient temperature for one hour. The reaction was diluted with water and the material was extracted with CH2Cl2, dried (Na2SO4), filtered and concentrated. Flash chromatography followed by trituration of the concentrated solid with EtOH gave 3-(6-chloro-3-methylpyridazin-4-yloxy)pyridin-2-amine (5.98 g, 25.3 mmol, 55%) as a solid.

Aufarbeitung

  1. extractionthe material was extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-26fdc25a0e444202a9bdfbe14c9feaac
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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