Potassium Carbonate → HCID 57629918, compound

Participants

Reaction Steps

A mixture of 5-bromopyrazin-2-amine (5 g, 29 mmol), pyrrolidin-2-one (11 mL, 144 mmol), copper (T) iodide (1.1 g, 5.75 mmol), potassium carbonate (7.94 g, 57.5 mmol), and (1R,2R)-cyclohexane-1,2-diamine (1.38 mL, 11.49 mmol) was refluxed under nitrogen in dioxane (100 mL) for 18 h. After cooling, 200 mL ethyl acetate and 20 mL methanol were added to the reaction. This was filtered through celite, concentrated, and absorbed onto sodium sulfate for purification by column chromatography (0-5% methanol/methylene chloride). The purified product was recrystallized from ether/ethyl acetate to afford 1-(5-aminopyrazin-2-yl)pyrrolidin-2-one (1.57 g, 8.81 mmol, 30.7% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.74 (1 H, d, J=1.51 Hz), 7.69 (1 H, d, J=1.51 Hz), 6.20 (2 H, s), 3.84 (2 H, t, J=7.05 Hz), 2.49 (2 H, t, J=7.93 Hz), 2.04 (2 H, dq, J=7.68, 7.51 Hz). MS (LC/MS) R.T.=0.48; [M+H]+=179.27.

Provenance & Evidence