Reacción #358599

Ecuación de reacción

water

4,6-dichloro-2-(methylthio)-5-phenylpyrimidine

4-chlorophenylboronic acid

Na2CO3

→

title compound

Rendimiento 35.1%

4-chloro-6-(4-chlorophenyl)-2-(methylthio)-5-phenylpyrimidine

Rendimiento 35.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   TemperaturaAfter cooling the reaction mixture to room temperature
3. 3
   ExtracciónThe resulting mixture was extracted with EtOAc (2×25 mL)
4. 4
   LavadoThe combined organic layers were washed with saturated aqueous NaCl
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by reverse phase preparative HPLC

Procedimiento

To a mixture of 4,6-dichloro-2-(methylthio)-5-phenylpyrimidine (2.71 g, 10.0 mmol), 4-chlorophenylboronic acid (1.72 g, 11.0 mmol) and tetrakis(triphenylphosphine)palladium (578 mg, 0.50 mmol) in toluene (25 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 10 mL, 20.0 mmol). The resulting reaction mixture was stirred at 100° C. under argon for 6 h, after which time analysis by HPLC/MS indicated that the reaction was complete. After cooling the reaction mixture to room temperature, water (50 mL) was added. The resulting mixture was extracted with EtOAc (2×25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to obtain 1.22 g of the title compound as a white solid. HPLC/MS: retention time=4.32 min, [M+H]30 =347.

Fuente