Triethylamine → 5,7-Dimethyl-2-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropyl)-[1,2,4]-triazolo[1,5-a]pyrimidine

Participants

Reaction Steps

To a solution of 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylic acid (70 mg, 0.289 mmol) in DMF (2.0 mL) was added 1-amino-4,6-dimethylpyrimidin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate (98 mg, 0.289 mmol) followed by O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (93 mg, 0.289 mmol) and triethylamine (0.040 mL, 0.289 mmol) at rt. After 2 h stirring at rt, the reaction mixture was stirred at 70° C. for 12 h. The crude product was purified by prep HPLC using Phenomenex column and MeOH—H2O-TFA as eluent (20% to 100% over 12 min gradient; flow: 40 mL/min) Collected the pure fractions and removed solvent. Obtained 5,7-dimethyl-2-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropyl)-[1,2,4]triazolo[1,5-a]pyrimidine as a white solid in 47% yield. Prepared hydrochloride salt by adding 1.0 M HCl and MeOH and removing solvent. 1H NMR (500 MHz, METHANOL-d4) δ 6.28 (s, 1H), 6.18-6.14 (m, 2H), 5.97 (s, 1H), 5.92-5.88 (m, 2H), 5.87-5.84 (m, 1H), 2.39 (s, 3H), 1.72-1.69 (m, 1H), 1.62-1.57 (m, 1H), 1.29-1.27 (m, 3H), 1.17 (s, 3H), 0.70 (dt, J=9.2, 6.1 Hz, 1H), 0.62-0.59 (m, 1H); MS (ESI) 345 (M+H); Rf=1.84 (Condition A).

Provenance & Evidence