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A mixture of 5 (2.67 g, 13.1 mmol), but-3-ynylamine HCl salt (2.76 g, 26.2 mmol) and potassium carbonate (3.62 g) in 40 ml of methanol was refluxed for 5 h. After the workup, the residue was purified by column chromatography (THF-EtOH=9:0.5) to give 2.2 g of yellow solid (6, 70% yield). 1H NMR (DMSO-d6, δppm): 2.26 (dt, 2H, ≡C—CH2—, J=7.2 Hz, 2.7 Hz), 2.50 (d, 2H, J=5.7 Hz), 2.63 (t, 2H, J=7.2 Hz), 2.78 (t, 1H, CH≡C—, J=2.7 Hz), 3.82 (m, 1H, HO—CH—), 4.25 (dd, 1H, imidazole-CHa—, J=13.8 Hz, 8.4 Hz), 4.54 (dd, 1H, imidazole-CHb—, J=13.8 Hz, 3.6 Hz), 5.13 (d, 1H, OH, J=5.1 Hz), 7.13 (s, 1H, —CH═), 7.55 (s, 1H, —CH═). 13C NMR (DMSO-d6, δppm): 18.80, 47.79, 52.04, 52.89, 68.09, 71.60, 82.87, 126.98, 128.19, 144.83.

1. temperaturewas refluxed for 5 h
2. customAfter the workup, the residue was purified by column chromatography (THF-EtOH=9:0.5)