N-Phenyl diethanolamine → HCID 76684686, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol (500 mg, 2.78 mmol), N-phenyldiethanolamine (458 mg, 2.53 mmol), tetrahydrofuran (5 mL) and a magnetic stirring bar were added to a 50 mL RBF. Triphenylphosphine (861 mg, 3.28 mmol) was added followed by the slow addition of diisopropylazodicarboxylate (664 mg, 3.28 mmol) via syringe over 15 minutes. The mixture was stirred at room temperature for 2 h. Progress of the reaction was monitored by HPLC. The reaction was concentrated then ethyl acetate (40 mL) was added which caused a precipitate to form. The precipitate was removed by filtration and rinsed with ethyl acetate (4 mL). The organic layer was concentrated. The title compound was purified by silica gel column chromatography with a gradient elution of 65-100% ethyl acetate in hexanes. Fractions were combined and concentrated under reduced pressure. The resulting solid was triturated with ethyl acetate (3 mL) and dried to afford the title compound as a white solid (274 mg, 32% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 7.16 (m, 3H), 6.90 (d, 2H), 6.59 (t, 1H), 4.71 (t, 1H), 3.73 (m, 2H), 3.56 (q, 2H), 3.46 (t, 2H), 3.35 (m, 2H), 2.74 (s, 3H), 2.56 (s, 3H). EM (calc.): 343.1; MS (ESI) m/e: 344.2 (M+H)+.

Provenance & Evidence