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

HRID 1809644

Reaction equation

HRID 1809644 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 866411083-(6-Chloro-3-methylpyridazin-4-yloxy)pyridin-2-amineYield 55.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-26fdc25a0e444202a9bdfbe14c9feaac
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Linked notes

Loading…