Triethylamine → HCID 25099660, compound

Participants

Reaction Steps

To a slurry of 4-amino-6-(4-fluoro-phenyl)-4,5-dihydro-2H-1,2,4-triazin-3-one (0.26 g, 1.23 mmol), 2-phenyl-pyrimidine-5-carboxylic acid (0.25 g, 1.23 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.37 g, 1.94 mmol) in DMF (12 mL) is added Et3N (0.2 mL, 1.435 mmol) under N2 and the reaction mixture is stirred at rt for 49 h. The mixture is diluted with EtOAc (120 mL), and washed successively with saturated aqueous NH4Cl (2×50 mL), water (2×50 mL), and saturated aqueous NaCl (50 mL). The organic phase is dried (MgSO4), filtered, and concentrated in vacuo. The residue is triturated with EtOH (30 mL) to afford 2-phenyl-pyrimidine-5-carboxylic acid [6-(4-fluoro-phenyl)-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl]-amide (0.12 g, 25%). MS: 391 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 11.25 (s, 1H), 10.58 (s, 1H), 9.31 (s, 2H), 8.47 (dd, J=7.7, 1.8 Hz, 2 H), 7.70-7.86 (m, 2 H), 7.49-7.67 (m, 3H), 7.18-7.34 (m, 2H), 4.77.

Provenance & Evidence