1,4-Dioxane hydrochloride → C-[4-(9H-Pyrimido[4,5-b]indol-4-yl)-morpholin-2-yl]-methylamine

Participants

Reaction Steps

A solution of [4-(9H-pyrimido[4,5-b]indol-4-yl)-morpholin-2-ylmethyl]-carbamic acid tert-butyl ester (0.021 g, 0.548 mmol) and 4M HCl-dioxane (1 mL) in methanol (5 mL) was stirred at room temperature for 2.5 hours. The solution was evaporated to dryness and purified by Ion exchange on SCX-II acidic resin (2 g) eluting with methanol, then 2 M ammonia-methanol. The basic fractions were combined. Preparative silica TLC, eluting with 1% ammonia—9% methanol—90% dichloromethane, gave the title compound (0.007 g, 0.025 mmol, 46%) as a beige powder. 1H NMR (500 MHz, CD3OD) δ 2.75-2.80 (2H, m), 3.00-3.06 (1H, m), 3.35-3.40 (1H, m), 3.75-3.85 (1H, m), 3.90 (1H, dd, J=10.10 Hz), 4.10-4.13 (1H, m), 4.19 (1H, d, J=13 Hz), 4.25 (1H, d, J=13 Hz), 7.35 (1H, dd, J=8.8 Hz), 7.47 (1H, dd, J=8.8 Hz), 7.57 (1H, d, J=8 Hz), 7.79 (1H, d, J=8 Hz), 8.46 (1H, s); LC-MS (3) Rt 1.98 min; m/z (ESI) 284 [MH+].

Provenance & Evidence