Sodium hydride → 3-[Cyano-(2,6-dimethoxy-5-nitro-pyrimidin-4-yl)-methyl]-5-methyl-benzonitrile

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2,6-dimethoxy-5-nitro-pyrimidine (0.45 g, 2.05 mmol, 1.05 eq., prepared according to Cushman et al. J. Org. Chem. 2004, 69, 601-612) and 3-cyanomethyl-5-methyl-benzonitrile (0.305 g, 1.95 mmol, 1.0 eq.) was dissolved in DMF (3.36 mL) and cooled to 0° C. 60% Sodium hydride (0.157 g, 3.92 mmol, 2.0 eq.) was added portionwise and the reaction was stirred at 0° C. for 1 h, then rt for 1 h. The reaction was cooled to 0° C. and quenched with saturated ammonium chloride solution. The pH was adjusted to ˜6.0 with 1N HCl and mixture was extracted with ethyl ether. The organic layer was washed with water (2×), dried (MgSO4) and concentrated. The resulting residue was purified by flash column chromatography (silica gel, 20 to 50% ethyl acetate/hexane) to give a yellow foam (0.6514 g, 98%). 1H NMR (300 MHz, CDCl3): δ 7.56 (s, 1H), 7.54 (s, 1H), 7.40 (s, 1H), 5.64 (s, 1H), 4.05 (s, 6H), 2.34 (s, 3H). Mass spectrum: 338.0 (M−H)−.

Provenance & Evidence