Methylamine → 2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-n-methyl-1,8-naphthyridine-3-methanamine

Participants

Reaction Conditions

Reaction Steps

A solution of methylamine in MeOH (8M, 1.06 ml, 8.46 mmol) was added to a mixture of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 1.0 g, 4.23 mmol) and methylamine hydrochloride (0.57 g, 8.46 mmol), in MeOH (20 ml) at room temperature. Sodium cyanoborohydride (1.06 g, 16.93 mmol) was then added and the reaction mixture heated at 70° C. for 2 h. Water was added to the cooled reaction mixture and the volume reduced under vacuum. The remaining predominantly aqueous phase was then extracted with DCM (3×), dried over Na2SO4 and evaporated to give the title compound. (UPLC-MS 7) tR 0.33; ESI-MS 252.2 [M+H]+.

Provenance & Evidence