[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[N:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.[O:14]1[C:16]([CH3:18])([CH3:17])[CH2:15]1.CC([O-])(C)C.[K+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]([CH2:15][C:16]([CH3:18])([OH:14])[CH3:17])[N:11]=[N:12][CH:13]=2)=[CH:4][CH:3]=1
6-Chloro-2-methyl-3-(1H-1,2,3-triazol-4-yl)pyridine (131 mg, 0.68 mmol) and 1,2-epoxy-2-methylpropane (65 μl, 0.71 mmol) were taken-up in DMF (2.7 ml). Potassium 2-methylpropan-2-olate (114 mg, 1.01 mmol) was added, and the mixture was heated to 60° C. for seven hours. Saturated aqueous ammonium chloride was added and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated, purified by reverse-phase HPLC (10-100% acetonitrile/water with 0.05% trifluoroacetic acid modifier). The appropriate fractions were neutralized with aqueous sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound.
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