Sodium hydride → 3-[(2,6-Bis-benzyloxy-5-ethyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrile

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Reaction Steps

To a stirred mixture of 2,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidine (39) (9.89 g, 27.87 mmol) and 3-Cyanomethyl-5-methyl-benzonitrile (4.15 g, 26.55 mmol) in anhydrous DMF (50 ml) in an ice-water bath under an atmosphere of nitrogen, was portionwise added 60% sodium hydride (2.34 g, 58.4 mmol). After stirring for 1 hr, the mixture was stirred at room temperature for overnight. The mixture was neutralized with aqueous saturated ammonium chloride solution. The crude product was extracted with ether and recrystallized from dichloromethane-hexane to afford 10.3 g (82%) a pale yellow solid; m.p. 139-141° C.; 1H NMR (200 MHz, CDCl3) δ: 1.00 (3H, t, J=7.6 Hz), 2.37 (3H, s), 2.52-2.58 (2H, m), 5.29 (1H, s), 5.49 (4H, s), 7.27-7.50 (10H, m); m/z (EI): 474 (M+).

Provenance & Evidence