Reacción #60829

Ecuación de reacción

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine

Intermediate 43

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine

thiophene-3-boronic acid

potassium carbonate

MgSO4

→

title compound

Rendimiento 82.0%

7-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine

Rendimiento 82.0%

Disolventes

toluene

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   OtroPurification by flash chromatography on silica eluting with 35% EtOAc/iso-hexane

Procedimiento

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 43) (50 mg), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (14 mg), thiophene-3-boronic acid (17 mg) and 2M potassium carbonate (0.25 mL) were heated in toluene (5 mL)/MeOH (1 mL) at 100° C. under an inert atmosphere. After 90 minutes the reaction mixture was cooled to ambient temperature, MgSO4 added, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 35% EtOAc/iso-hexane gave the title compound as a colourless solid (40 mg, 82%);

Fuente