Iodoethane → HCID 70874168, compound

Participants

Reaction Steps

A solution of methyl 3-methyl-2-[(oxan-4-yl)amino]pyridine-4-carboxylate (67 mg, 0.27 mmol) in dry DMF (1.0 ml), was added to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 16 mg, 0.4 mmol) in DMF (0.3 ml) at 0° C. under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. The reaction was then treated with iodoethane (16 μl, 0.20 mmol) and stirred for 30 minutes, and then treated again with iodoethane (16 μl, 0.20 mmol) and stirred for a further 30 minutes. The reaction mixture was added to a suspension of sodium hydride (16 mg, 0.4 mmol) in DMF (0.3 ml) at 0° C. Once addition was complete, the reaction mixture was allowed to reach room temperature and stirred for 1 hour before treating with iodoethane (2×16 μl, 0.40 mmol). The reaction mixture was stirred for a further 30 minutes. Sodium hydride (16 mg, 0.4 mmol) was added to the reaction mixture and the mixture stirred for 45 minutes before treating with iodoethane (2×16 μl, 0.40 mmol) and stirred for 15 minutes before adding under nitrogen to a solution of 4M HCl/dioxane (5.0 ml) with cooling.

Provenance & Evidence