Benzene, 2-iodo-1,3-dimethyl- → (E)-9-(2,6-dimethylstyryl)-2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

To an oven-dried 50 mL round-bottom flask were added 2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine (0.32 g, 0.93 mmol), Pd(OAc)2 (10 mg, 0.05 mmol), tri-o-tolylphosphine (30 mg, 0.1 mmol), 2-iodo-m-xylene (0.39 g, 1.67 mmol). The mixture was flushed with Ar and then dissolved in ˜10 mL anhydrous DMF. DIEA (0.39 g, 2.79 mmol) was then added via syringe. The reaction was stirred at 110° C. overnight. The reaction was diluted with EtOAc and filtered through celite, washed with ample ˜5% MeOH/EtOAc, the combined organic layer was washed with water twice, dried over Na2SO4. Final product was purified by silica gel column chromatography (4˜8% MeOH/DCM).

Provenance & Evidence