Into a sealable tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-{[3-(methyloxy)phenyl]methyl}-3-piperidinecarboxamide (186 mg, 0.392 mmol), EtOH (5 mL), Hunig's base (0.068 ml, 0.392 mmol), and hydrazine anhydrous (0.074 mL, 2.35 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. When the temperature of the reaction reached to 100° C., the solid in the mixture was all dissolved. After overnight, there was a yellow solution as well as a little amount of black colored solid formed. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid was filtered from the yellow solution. Water (20 mL) was added to the yellow solution, and a solid was formed. The solid was filtered, washed by water, and dried in vacuum. The solid was recrystallized from CH3CN, and the solid was filtered, washed by CH3CN, and dried in vacuum to afford the title compound (31 mg) as a light yellow solid. LC-MS (ES) m/z=487 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.16 (d, J=6.8 Hz, 3H), 1.58-1.71 (m, 2H), 1.76 (m, 1H), 1.86 (m, 1H), 2.36 (m, 1H), 3.75 (s, 3H), 4.19 (m, 1H), 4.23 (m, 1H), 4.33 (m, 1H), 4.37 (m, 1H), 5.38 (s, 2H), 6.08 (s, 2H), 6.59 (s, 1H), 6.81-6.91 (m, 3H), 7.26 (m, 1H), 7.52-7.63 (m, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.94 (s, 1H), 8.48 (m, 1H), 11.50 (s, 1H).
