(Z)-Benzaldehyde oxime → HCID 75985010, compound

Participants

Reaction Steps

To a suspension of sodium hydride (NaH, 60% dispersion in mineral oil; 0.037 g, 0.91 mmol) in DMF (2 mL) was added a solution of benzaldehyde oxime (0.125 g, 1.04 mmol) in DMF (1 mL), and the resulting frothy mixture was stirred for 1 h. To the resulting pale yellow mixture was added a solution of N′-(5-fluoro-2-methanesulfonylpyrimidin-4-yl)-N,N-dimethylformamidine (0.15 g, 0.61 mmol) in DMF (1 mL), and the homogeneous, pale-yellow solution was stirred at 25° C. for 16 h. The reaction mixture was diluted with H2O (50 mL) and was extracted with CH2Cl2 (2×100 mL). The organic extracts were combined, washed with H2O (5×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to a colorless oil. Trituration with Et2O afforded N′-{5-fluoro-2-[1-phenylmethylideneaminooxy]pyrimidin-4-yl}-N,N-dimethylformamidine (0.054 g, 31%) as a white solid: mp 240-244° C. dec; 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 8.53 (s, 1H), 8.19 (d, J=2.4 Hz, 1H), 7.81-7.69 (m, 2H), 7.49-7.30 (m, 3H), 3.21 (s, 3H), 3.21 (s, 3H); ESIMS m/z 288 ([M+H]+).

Provenance & Evidence