Hydrochloric Acid → 6-(2,4-difluorophenyl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

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Reaction Steps

A mixture of 1-(2,4-difluorophenyl)-2-phenylethanone (Intermediate 21) (250 mg, 1.1 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (189 mg, 0.90 mmol), urea (162 mg, 2.69 mmol), and concentrated HCl solution (0.075 mL, 0.90 mmol) in EtOH (10 mL) was refluxed overnight. The mixture was evaporated in vacuo, and the residue was purified by preparative HPLC to give Compound 49 (30.03 mg, yield 7%). 1H NMR (DMSO-d6 400 MHz): δ 10.32 (s, 1H), 8.91 (s, 1H), 7.57 (s, 1H), 7.49 (s, 1H), 7.43-7.37 (m, 1H), 7.29 (s, 1H), 7.11-6.89 (m, 5H), 6.88 (d, J=7.2 Hz, 2H), 5.27 (s, 1H), 4.08 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.2 Hz, 3H); MS (ESI): m/z 468.1 [M+1]+.

Provenance & Evidence