Sodium hydride → (3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

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Reaction Steps

To a stirred mixture of 4-Chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (23.8 g, 0.11 mol) and (3-Chloro-5-methyl-phenyl)-acetonitrile (47) (16.6 g, 0.1 mol) in anhydrous DMF (200 ml) in an ice-water bath under an atmosphere of nitrogen, was portionwise added 60% sodium hydride (8.8 g, 0.22 mol). 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 purified by silica gel column chromatography (eluent, EA:hexane (1:10)) to afford 24 g (69%) of a white solid. m.p. 105-106° C.; 1H NMR (200 MHz, CDCl3) δ: 1.11 (3H, d, J=7.1 Hz), 1.15 (3H, d, J=7.1 Hz), 2.32 (3H, s), 3.00 (1H, m), 4.00 (3H, s), 4.02 (3H, s), 5.33 (1H, s), 7.10-7.16 (3H, m).

Provenance & Evidence