cis-4-[5-Bromo-4-(2-methyl-3-furanyl)-2-pyrimidinyl]-2,6-dimethylmorpholine (100 mg, 0.284 mmol), 3-methyl-4-pyridinyl)boronic acid HCl (54.2 mg, 0.312 mmol), sodium carbonate (75 mg, 0.710 mmol) and tetrakis(triphenylphosphine)palladium(0) (16.40 mg, 0.014 mmol) were added together in 1,4-dioxane (3 mL) and water (0.500 mL) and the resulting mixture was heated at 85° C. under argon for 4 hours. A further amount of (3-methyl-4-pyridinyl)boronic acid HCl (54.2 mg, 0.312 mmol), sodium carbonate (75 mg, 0.710 mmol) and tetrakis (16.40 mg, 0.014 mmol) were added and the resulting mixture was heated at 85° C. under argon for 18 hours. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (×3). The ethyl acetate layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by Biotage SP4 column chromatography eluting with a gradient of 0-60% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure. The residue was dissolved in methanol (1 ml), treated with 1M HCl in ether (0.1 mL, 0.100 mmol) and evaporated under reduced pressure. The resulting solid was dried under high vacuum at 40° C. for 18 hours to give the title compound (34 mg, 0.085 mmol, 29.9% yield) as a white solid. LC/MS [M+H]+=365; 1H NMR (400 MHz, d4-MeOD): δ 8.68-8.66 (2H, m), 8.33 (1H, s), 7.92-7.90 (1H, d), 7.25-7.24 (1H, d), 5.75-5.74 (1H, d), 4.74-4.70 (2H, m), 3.72-3.64 (2H, m), 2.73-2.67 (2H, m), 2.49 (3H, s), 2.18 (3H, s), 1.25-1.24 (6H, m).
