Ammonium Hydroxide → 2-(1-Benzyl-4-methyl-pyrrolidin-3-yl)-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Participants

Reaction Conditions

Reaction Steps

To a 300 mL sealed tube was added a mixture of compound 4 (4.7 g, 13.7 mmol), NH4OAc (11 g, 14.3 mmol) and ammonium hydroxide (50 mL) in MeOH (120 mL). The reaction mixture was stirred at 130° C. for 2 days. After cooling down, the reaction mixture was concentrated in vacuo. The residue was diluted with CH2Cl2 (100 mL) and washed with water (50 mL×2). The organic phase was separated and dried over Na2SO4. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluted with DCM/MeOH=50:1 to 30:1) to afford compound 5 (1.8 g, 40.6% yield) as a white solid. LC-MS: m/z 310.17 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 8.02 (s, 1H), 7.85 (s, 1H), 7.39˜7.28 (m, 5H), 3.82 (d, J=12.4 Hz, 1H), 3.58 (d, J=12.4 Hz, 1H), 3.41˜3.37 (m, 1H), 2.99 (d, J=6.4 Hz, 1H), 2.72˜2.70 (m, 1H), 2.54˜2.50 (m, 1H), 2.44˜2.40 (m, 1H), 1.95˜1.91 (m, 1H), 1.20 (d, J=6.4 Hz, 3H).

Provenance & Evidence