N,N-Dimethylaniline → HCID 89437205, compound

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Reaction Steps

The 2-amino-5-bromopyrazine (commercially available, 0.687 g, 1.0 eq.) was dissolved in tetrahydrofuran (10 mL). Then N,N-dimethylaniline (500 μL, 1.0 eq.) and methyl-4-chloro-4-oxo-butanoate (535 μL, 1.1 eq.) was successively added. The mixture was refluxed for 12 h. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer were dried on magnesium sulfate and concentrated under vacuum. The residue was purified by flash chromatography eluting with cyclohexane-ethyl acetate to give methyl 4-[(5-bromopyrazin-2-yl)amino]-4-oxo-butanoate A2 (70%). 1H NMR (400 MHz, DMSO-d6) δ 11.02 (bs, 1H), 9.12 (s, 1H), 8.62 (s, 1H), 3.60 (s, 3H), 2.74 (t, 2H), 2.62 (t, 2H) ppm. LC-MS (Method A): RT 1.28, 290 (M+H+)

Provenance & Evidence