Benzaldehyde → 7-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-2-phenyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

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Reaction Steps

A mixture of {6-[2-(3,-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidin-4-yl}-hydrazine (131) (60 mg, 0.18 mmol), benzaldehyde (21 mg, 0.2 mmol) in EtOH is refluxed for 4 hours. Solvent is removed in vacuo. HOAc (2 mL) is added to the residue, and then bromine (0.3 mmol) is slowly added. The mixture is stirred at room temperature overnight. Solvent is removed in vacuo and the residue is treated with NaHCO3 (aq) and DCM. The organic layer is separated and the aqueous layer is extracted with DCM (2×0 mL). The combined organic layers are dried (MgSO4), the solvent is removed, and the crude purified by PTLC (10% MeOH in DCM) to give a white solid; 1H-NMR (CDCl3) δ: 8.93 (s, 1H), 8.44 (dd, 1H), 7.78–7.88 (m, 2H), 7.51–7.63 (m, 4H), 7.22–7.36 (m, 3H), 5.82 (s, 2H), 3.05 (q, 2H), 1.70–1.80 (m, 2H), 1.02 (t, 3H).

Provenance & Evidence