[CH:1]1([C:4]2[N:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.[O-:12][CH2:13][CH3:14].[Na+].C(OCC)C.[Cl-].[NH4+]>C(O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10](=[NH:11])[O:12][CH2:13][CH3:14])[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1To a solution of 2-cyclopropylpyrimidine-4-carbonitrile (20.97 g, 144.5 mmol) in ethanol (100 mL) was added sodium ethoxide (1.8 g, 78.9 mmol of sodium metal in 30 mL of ethanol). The reaction mixture was stirred at room temperature for 30 minutes. Diethyl ether (300 mL) was added to the reaction mixture followed by a saturated aqueous solution of ammonium chloride (50 mL). The mixture was extracted with diethyl ether (100 mL×3). The combined organics were washed with brine (50 mL×2), dried over magnesium sulfate, filtered, concentrated under reduced pressure and dried under high vacuum to afford the title compound. The material was used without further purification. 1H NMR (500 MHz, CDCl3) δ 1.10-1.15 (m, 2H), 1.16-1.22 (m, 2H), 1.43 (t, 3H), 2.32 (tt, 1H), 4.44 (q, 2H), 7.50 (d, 1H), 8.72 (d, 1H).
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