To a microwave vial, was added 2-chloro-5-fluoro-N-(((1S,9aR)-octahydro-1H-quinolizin-1-yl)methyl)pyrimidin-4-amine (prepared according to Example 1; 400 mg, 1.34 mmol, 1 equiv), 1-(5-amino-2-(oxetan-3-yloxy)phenyl)-4-methyl-1H-tetrazol-5(4H)-one (prepared as described in WO2011/068898, the disclosure of which is incorporated herein by reference; 493 mg, 1.87 mmol, 1.4 equiv), rac-BINAP (181 mg, 0.291 mmol, 0.217 equiv), Cs2CO3 (1.31 g, 4.02 mmol, 3 equiv), Pd(OAc)2 (26 mg, 0.116 mmol, 0.0870 equiv), and dioxane (10 mL). The microwave vial was capped and sonicated under vacuum for 5 min. The reaction mixture was heated in the microwave at 120° C. for 2 h. The cooled reaction mixture was filtered using a pad of celite and rinsed with dioxane, and the filtrate was concentrated. The crude product was purified by flash chromatography and eluted with DCM:2M NH3/MeOH=100:0 to 94:4 using 1% 2M NH3/MeOH increments to provide the desired product Compound 14 1-(5-(4-(((1S,9aR)-octahydro-1H-quinolizin-1-yl)methylamino)-5-fluoropyrimidin-2-ylamino)-2-(oxetan-3-yloxy)phenyl)-4-methyl-1H-tetrazol-5(4H)-one (535 mg, 76%) as a solid.
