Reaktion #87389

Reaktionsgleichung

2-Chloro-4-(1-ethoxyvinyl)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

2-(dicyclohexylphosphino)biphenyl

cesium carbonate

→

title compound

Ausbeute 48.0%

4-(1-Ethoxyvinyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine

Ausbeute 48.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was capped
2. 2
   Sonstigeevacuated
3. 3
   Sonstigeflushed with nitrogen
4. 4
   FiltrationThe mixture was filtered through a pad of silica
5. 5
   Waschenthe silica was washed by 5% of MeOH in DCM
6. 6
   SonstigeThe solvents were evaporated
7. 7
   Sonstigethe residue was purified by preparative HPLC

Vorschrift

2-Chloro-4-(1-ethoxyvinyl)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (70 mg, 0.23 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (46 mg, 0.23 mmol), palladium(II) acetate (8 mg, 0.03 mmol), 2-(dicyclohexylphosphino)biphenyl (12 mg, 0.03 mmol) and cesium carbonate (147 mg, 0.45 mmol) were mixed in dioxane (4 mL). The vial was capped, evacuated and flushed with nitrogen. The reaction mixture was heated by microwave irradiation at 120° C. for 1.5 h. The mixture was filtered through a pad of silica and the silica was washed by 5% of MeOH in DCM. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound 52 mg (48%).

Quelle