Sodium hydride → HCID 59686842, compound

Participants

Reaction Steps

2,4-bis(benzyloxy)-6-chloro-5-isopropylpyrimidine (45.4 g, 0.123 M) and 3-(cyanomethyl)-5-methylbenzonitrile (18.3 g, 0.117 M) were dissolved in anhydrous DMF (200 mL). After cooling the mixture in an ice bath under nitrogen atmosphere, 60% sodium hydride (9.38 g, 0.235 M) was added portionwise (addition time ca. 1.5 hr.). The mixture was stirred for further 1 hr. in an ice bath and stirred for ca. 20 hr. at room temperature. The reaction mixture was then cooled in an ice bath and sat. aqueous ammonium chloride solution was added thoroughly. The crude product was extracted with ether, washed with water twice, dried with magnesium sulfate, filtered, and evaporated in vacuo to give a light brown syrup, which was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:9)) to afford 53.46 g (94%) of 3-((2,6-bis(benzyloxy)-5-isopropylpyrimidin-4-yl) (cyano)methyl)-5-methylbenzonitrile as a light brown syrup. λmax (film) 2236 (nitrile) cm−1, 1H NMR (200 MHz, CDCl3) δ 1.10 (3H, d, J=6.9 Hz), 1.12 (3H, d, J=6.9 Hz), 2.36 (3H, s), 2.96 (1H, m), 5.37 (1H, s), 5.44 (4H, s), 7.32-7.55 (13H, m).

Provenance & Evidence