[CH2:1]([C:3]1[C:4]([O:15]C)=[N:5][C:6]([CH3:14])=[C:7]([C:9]2[O:10][CH:11]=[N:12][N:13]=2)[CH:8]=1)[CH3:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[O:10][CH:11]=[N:12][N:13]=2)[CH:8]=1)[CH3:2]To a mixture of 3-ethyl-2-methoxy-6-methyl-5-[1,3,4]oxadiazol-2-yl-pyridine (10 mg, 0.0457 mmol) and sodium iodide (19 mg, 0.127 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (2 mL) followed by chlorotrimethylsilane (16.4 μL, 0.131 mmol). The reaction mixture is stirred at 50° C. under nitrogen for 2.5 hr. The reaction mixture is allowed to cool and then quenched with water (0.1 mL). After stirring for 30 min, the mixture is evaporated. The crude residue is purified by flash chromatography on a 2-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). The fraction containing the product is evaporated to give 3-ethyl-6-methyl-5-(1,3,4-oxadiazol-2-yl)-1H-pyridin-2-one (2 mg, 21% yield) as a white solid. LC/MS: RT: 1.98 min, MS: m/e=206 (M+H).
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