Hydrochloric Acid → HCID 59548351, compound

Participants

Reaction Steps

5-(1,3-Dioxolan-2-yl)-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-amine (3.042 g, 6.21 mmol) was dissolved in tetrahydrofuran (50 mL) and then 2.0 M hydrochloric acid (15.5 mL, 31.0 mmol) was added via syringe, followed by a THF rinse (1.5 mL). The reaction was stirred at room temperature for 20 minutes, diluted with water (20 mL), and filtered. The solid was washed with water, collected, and dried under high vacuum over the weekend to afford 6-(6-methoxypyridin-3-ylamino)-5-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)nicotinaldehyde (1.7 g, 61% yield). MS (ESI pos. ion) m/z 446 (M+H)+. 1H NMR (CDCl3, 400 MHz) δ 13.33 (s, 1H), 10.29 (d, J=2.15 Hz, 1H), 10.00 (s, 1H), 8.78 (d, J=1.96 Hz, 1H), 8.48 (d, J=2.74 Hz, 1H), 8.35 (s, 1H), 8.25 (dd, J=8.8 Hz, 2.74 Hz, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.89 (dd, J=10.47 Hz, 2.05 Hz, 1H), 4.23 (d, J=11.74 Hz, 1H), 3.98 (s, 3H), 3.88-3.82 (m, 1H), 2.93 (s, 3H), 2.23-2.03 (m, 3H), 1.90-1.65 (m, 3H).

Provenance & Evidence