Sodium Hydroxide → 2-(((5-Aminopyridin-2-yl)methyl)(methyl)amino)ethanol

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 40 (400 mg, 1.1 mmol) in conc. sulfuric acid (1.3 mL) was heated at 50° C. for 3 h. The reaction mixture was cooled to 0° C., basified with 2N NaOH solution (15 mL) to pH ˜9 and extracted with 10% MeOH/CHCl3 (2×100 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated to obtain the desired amine (100 mg, 50%) as a brown liquid. Rf: 0.4 (10% MeOH/CHCl3, alumina plate); (m/z): 182 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 7.82 (1H, d, J=2.4 Hz), 7.05 (1H, d, J=8.4 Hz), 6.87 (1H, dd, J=2.8, 8.0 Hz), 5.15 (2H, s), 4.38 (1H, br s), 3.47-3.43 (4H, m), 2.42 (2H, t, J=6.4 Hz), 2.15 (3H, S).

Provenance & Evidence