Reacción #87389

Ecuación de reacción

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

Rendimiento 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

Rendimiento 48.0%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe vial was capped
2. 2
   Otroevacuated
3. 3
   Otroflushed with nitrogen
4. 4
   FiltraciónThe mixture was filtered through a pad of silica
5. 5
   Lavadothe silica was washed by 5% of MeOH in DCM
6. 6
   OtroThe solvents were evaporated
7. 7
   Otrothe residue was purified by preparative HPLC

Procedimiento

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%).

Fuente