Formaldehyde → 2-(2-(2-(2-((6-(1-Methylpiperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

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To a mixture of 2-(2-(2-(2-((6-(piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide 62 (0.064 g, 0.13 mmol) in anhydrous MeOH (2.0 mL) was added 37% aqueous formaldehyde (0.04 mL, 0.5 mmol) and sodium triacetoxyborohydride (0.138 g, 0.649 mmol). The mixture was stirred for 3 hours at room temperature under a nitrogen atmosphere and then quenched by the addition of sat. aq. NaHCO3 (30 mL). The aqueous phase was extracted with EtOAc (2×20 mL), the combined organics were dried using a phase separation cartridge and then concentrated under reduced pressure. The organic residues were purified by prep-LCMS to give the title compound 63 (0.020 g, 30%) as the formic acid salt (2 equivs. determined by 1H NMR). LCMS-A: rt 4.786 min; m/z 513.3 [M+H]+.

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