Iodine → 2-(1-Benzyl-4-methyl-pyrrolidin-3-yl)-7-iodo-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 5 (1.0 g, 3.24 mmol) in dry THF (70 mL) was added n-BuLi (2.5 M, 2 mL) dropwise at −78° C. over 30 minutes. The reaction was stirred at −45° C. for 30 minutes. Then a solution of iodine in THF (20 mL) was dropwise added at −78° C. over 10 minutes. The resulting mixture was stirred at 0° C. for 2 hours. The reaction was quenched with saturated aqueous Na2S2O3 solution (10 mL). Then the reaction mixture was diluted with EtOAc (200 mL), and washed with brine (50 mL×2). The separated organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluted by PE/EtOAc=10:1 to 2:1) to afford compound 6 (930 mg, 66% yield) as a white solid. LC-MS: m/z 435.99 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 1H), 7.37˜7.26 (m, 5H), 3.82 (d, J=12.4 Hz, 1H), 3.59 (d, J=12.4 Hz, 1H), 3.42˜3.38 (m, 1H), 2.98 (d, J=8.4 Hz, 1H), 2.82˜2.81 (m, 1H), 2.55˜2.51 (m, 1H), 2.45˜2.42 (m, 1H), 1.96˜1.92 (m, 1H), 1.22 (d, J=7.2 Hz, 3H).

Provenance & Evidence