[NH:1]1[CH:5]=[N:4][C:3]([C:6]#[N:7])=[N:2]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>ClCCCl>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:1]1[CH:5]=[N:4][C:3]([C:6]#[N:7])=[N:2]1To a solution of 1H-1,2,4-triazole-3-carbonitrile (1.00 g, 10.63 mmol) in DCE (10 mL) was added 3,4-dihydro-2H-pyran (1.94 ml, 21.26 mmol) and p-toluenesulfonic acid (183 mg, 1.06 mmol). The resulting mixture was stirred at room temperature under nitrogen for 15 minutes. Saturated aqueous sodium bicarbonate solution (25 mL) was added and the product extracted into DCM (25 mL×3). The combined organics were washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage, 0-10% methanol gradient in DCM) to give the title intermediate as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 1.81-1.63 (3H, m), 2.11-1.95 (2H, m), 2.19 (1H, dd, J=8.1, 5.6 Hz), 3.87-3.65 (1H, m), 4.18-3.97 (1H, m), 5.53 (1H, dd, J=8.5, 2.9 Hz), 8.37 (1H, s).
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