To a solution of 4-{2-amino-6-[(3R)-3-(1-methylethyl)-4-morpholinyl]-4-pyrimidinyl}-2-(ethyloxy)-6-fluorobenzonitrile (370 mg, 0.96 mmol) in ethanol (10 mL) was added hydrazine monohydrate (2.0 mL) in one portion. The mixture was heated at 100° C. for 20 hours. LCMS showed conversion complete. The mixture was cooled to room temperature and concentrated in vacuo. The solid residue was partitioned between EtOAc (2×40 mL) and water (15 mL). The organic was concentrated in vacuo, and the residue was purified by silica gel column chromatography using gradient elution of 1% A in CHCl3 to 75% A in CHCl3, where A was a mixture of 800/80/3200 (v/v/v) CH3OH/NH4OH/CHCl3. The collected fractions were concentrated in vacuo. The residue was redissolved in CHCl3 and EtOAc, followed by filtration. The filtrate was concentrated in vacuo, and azeotroped with EtOH. The residue was taken up in water (8 mL) as a suspension. The solids were collected by filtration and washed with water (2×2 mL), drying under house vacuum at room temperature for 1 hour and then drying under vacuum at room temperature over P2O5 for 20 hours. These solids were washed with hexane (2×3 mL), and dried under vacuum at 65° C. for 20 hours to afford the title compound (273 mg) as an off-white solid. LC-MS (ES) m/z=398 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 0.87 (d, J=6.8 Hz, 3H), 1.10 (d, J=6.6 Hz, 3H), 1.54 (t, J=7.1 Hz, 3H), 2.44-2.54 (m, 1H), 3.21-3.30 (m, 1H), 3.50-3.59 (m, 2H), 3.92 (dd, J=11.2, 3.4 Hz, 1H), 4.09 (d, J=11.9 Hz, 1H), 4.30 (q, J=6.9 Hz, 2H), 6.41 (s, 1H), 6.83 (s, 1H), 7.30 (d, J=1.0 Hz, 1H).
