Cesium carbonate → Methyl 4'-(2-(4-cyanophenylamino)-9-methyl-9H-purin-6-yloxy)-3',5'-dimethylbiphenyl-4-carboxylate

Participants

Reaction Steps

A degassed solution of methyl 4′-(2-chloro-9-methyl-9H-purin-6-yloxy)-3′,5′-dimethylbiphenyl-4-carboxylate (180 mg, 0.43 mmol), 4-aminobenzonitrile (105 mg, 0.89 mmol), Pd(OAc)2 (10 mg, 0.044 mmol), BINAP (57 mg, 0.092 mmol), and Cs2CO3 (280 mg, 0.88 mmol) in toluene (2 mL) was heated at 80° C. overnight. The desired product was precipitated with EtOAc (2 mL) and saturated NaHCO3 (2 mL) and the resulting precipitate was collected by filtration (210 mg). NMR (DMSO-d6): δ 10.10 (s, 1H), 8.25 (s, 1H), 8.10 (d, 2H), 7.95 (d, 2H), 7.68 (s, 2H), 7.60 (d, 2H), 7.34 (d, 2H), 3.91 (s, 3H), 3.80 (s, 3H), 2.18 (s, 6H); MS (ESI): m/z 505 (M+1)+.

Provenance & Evidence