2-(Dimethylamino)ethanol → 2-[(5-Bromopyrazin-2-yl)oxy]-N,N-dimethylethan-1-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(dimethylamino)ethanol (28-1, 8.00 g, 78.9 mmol) in THF (100 mL) was added sodium tert-butoxide (10.0 g, 102.0 mmol) at room temperature. The reaction was stirred for 15 min. The reaction mixture was cooled to 0° C. and added with a solution of 2,5-dibromopyrazine (28-2, 20.0 g, 82.4 mmol) in THF (100 ml) slowly in a period of 5.0 min. The reaction mixture was warmed to room temperature and stirred for 16 h. The mixture was diluted with ethyl acetate and washed with saturated NH4Cl. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give 2-((5-bromopyrazin-2-yl)oxy)-N,N-dimethylethanamine (28-3, 17.0 g) as yellow oils in 88% yield: 1H NMR (500 MHz, CDCl3) δ 8.46 (s, 1 H), 8.16 (d, J=1.1 Hz, 1 H), 8.06 (d, J=1.1 Hz, 1 H), 4.68 (t, J=4.8 Hz, 2 H), 3.20 (s, 2 H), 2.70 (s, 6 H).

Provenance & Evidence