Toluene → 3-Benzylpyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of N,N,N′,N′-tetramethylethylendiamine (TMEDA, 15.00 mL, 0.10 mol) in toluene (22.00 mL, 0.21 mol) at 0° C., buthyllitium 1.6M in n-hexane (63.00 mL, 0.10 mol) was added dropwise. Then the mixture was heated at 60° C. and after 30 min was slowly added to a cooled solution of 2-aminopyrazine 11 (2.00 g, 0.02 mol) in anhydrous THF (20 mL). The reaction mixture was stirred at 0° C. for 30 min, poured into ice and extracted with ethyl acetate (3×20 mL). The organic layer was dried over Na2SO4, filtered and the solvent removed under reduced pressure. The crude was purified by flash chromatography (EtOAc, dichloromethane; 65:35) to get 1.38 g (35% yield) of the title compound 12 as a yellow solid (mp 93-96° C.). 1H-NMR (CDCl3): 4.08 (s, 2H), 4.33 (br s, 2H), 7.18-7.35 (m, 5H), 7.91 (m, 2H). MS (ESI): m/z 186 (M+H−).

Provenance & Evidence