Into a sealed tube, (3S,6R)-1-[6-(4-acetyl-3-fluorophenyl)-2-amino-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide (90 mg, 0.195 mmol), O-methylhydroxylamine hydrochloride (16.3 mg, 0.20 mmol), and K2CO3 (32.3 mg, 0.234 mmol) were stirred together in DME (3 mL) for 4 hours at 57° C. The reaction mixture was filtered, and the filtrate containing the oxime intermediate was concentrated in vacuo to 2 mL. Then EtOH (3 mL), Hunig's base (0.05 mL, 0.27 mmol), and hydrazine anhydrous (0.013 mL, 0.410 mmol) were added, and the resulting yellow mixture was heated overnight at 120° C. in an oil bath. The solution turned black. LCMS showed mainly product. The black solid was filtered and the yellow filtrate was evaporated. The resulting yellow residue was dissolved in CH3OH, and purified by HPLC (CH3CN/H2O w/0.1% HCO2H) to afford a formic acid salt of the title compound (9 mg) as a light yellow solid. LC-MS (ES) m/z=456 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 1.32 (m, 4H), 1.75-1.91 (m, 3H), 1.97-2.12 (m, 1H), 2.41-2.53 (m, 1H), 2.60 (s, 3H), 3.11-3.27 (m, 1H), 4.33-4.50 (m, 2H), 4.56-4.74 (m, 1H), 6.59 (s, 1H), 7.23-7.41 (m, 5H), 7.54-7.63 (m, 1H), 7.96 (m, 1H), 7.94 (s, 1H).
