Triethylamine → 6-Methoxy-2,5-dimethylpyridin-3-amine

Participants

Reaction Steps

To a solution of 2-(dibromomethyl)-6-methoxy-5-methyl-3-nitropyridine (110 g, 0.323 mol) from Part J, in EtOH (1.1 L) in a Parr bottle was added triethylamine (135 mL, 0.970 mol) followed by 10% Pd/C (11.0 g). The mixture placed on a Parr shaker under an H2 atm at 45 psi for 18 h. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was partitioned between water and EtOAc and the organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (10%→20%→35%→50% ethyl acetate in hexanes) to give 6-methoxy-2,5-dimethylpyridin-3-amine (35.7 g, 73% yield) as a light-brown solid: mp 39.8-41° C.; 1H NMR (400 mHz, DMSO-d6) δ 6.82 (s, 1H), 4.37 (s, 2H), 3.73 (s, 3H), 2.16 (s, 3H), 2.00 (s, 3H); 13C NMR (100 mHz, DMSO-d6) δ 152.7, 135.8, 134.8, 126.3, 116.1, 52.1, 19.2, 14.7; LRMS, (ESI) m/e 153.2 [(M+H)+, calcd for C8H13N2O, 153.1].

Provenance & Evidence