[Si]([C:5]#[N:6])(C)(C)C.CN(C)NC(Cl)=O.[CH2:14]([NH:16][C:17]1[CH:18]=[N+:19]([O-])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[CH3:15]>CN(C=O)C.C(Cl)Cl.O>[CH2:14]([NH:16][C:17]1[C:18]([C:5]#[N:6])=[N:19][CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[CH3:15]TMSCN (1.1 ml, 8.33 mmol) and dimethyl amino carbamoyl chloride (0.76 mL, 8.33 mmoL) are added to a solution of 3-ethylamino-4-nitro-pyridine-1-oxide (1 g, 6.94 mmol) in anhydrous DMF (10 mL) were added. The reaction mixture is stirred overnight at 80° C., cooled to room temperature, and diluted with CH2Cl2 and water. The combined organic layer is washed with water, brine, dried over Na2SO4, and concentrated. The residue is chromatographed eluting with 40% EtOAc-hexanes to afford 3-ethylamino-4-nitro-pyridine-2-carbonitrile as a yellow solid. 1H NMR (300 MHz, CD3OD): δ 7.82 (d, J=4.5 Hz, 1H), 7.50 (d, J=4.5 Hz, 1H), 3.70 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H).
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