Water → Tert-butyl 2-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-YL)-6-fluoropyridin-3-YL)acetate

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To 4-chloro-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.783 g, 2.035 mmol) (Example 51), tert-butyl 2-(6-fluoro-5-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)pyridin-3-yl)acetate (1.49 g, 4.07 mmol), and bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.072 g, 0.102 mmol) was added dioxane (20 mL) and potassium carbonate in water (3.05 mL, 6.10 mmol), and the resulting mixture was heated at 80° C. for 1 h. The reaction mixture was then added to a separatory funnel and partitioned between EtOAc (100 mL) and sodium bicarbonate (saturated, aqueous). The organic layer was separated, washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel; 0% to 40% EtOAc/hexanes) gave the title compound (37% yield). m/z (ESI, +ve ion) 560.4 (M+H)+.

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