To a stirred solution of 5-bromo-2-morpholinopyridin-3-amine (0.5 g, 1.94 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.074 g, 0.16 mmol), Pd2dba3 (0.071 g, 0.08 mmol) and 3-methylmorpholine (0.98 g, 9.7 mmol) in THF (3.9 mL). To this mixture was added LHMDS in THF (1.0 M, 10.65 mL, 10.65 mmol) and the resulting reaction was heated to 65° C. The reaction was stirred for 2.25 h. After which, the reaction was cooled to rt and then poured into water (50 mL) and extracted with EtOAc (2×50 mL) and DCM (2×50 mL). The combined organic layers were dried over magnesium sulfate and the crude product was purified on basic alumina (0-100% EtOAc/hexane) to give 5-(3-methylmorpholino)-2-morpholinopyridin-3-amine. Mass Spectrum (ESI) m/e=279.2 (M+1).
