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

Participants

Reaction Steps

To a solution of compound 6 (70 mg, 0.296 mmol) and potassium carbonate (70 mg, 0.296 mmol) in acetonitrile (10 mL) was added benzyl bromide (70 mg, 0.296 mmol). The resulting solution was stirred at room temperature for 2 h. LC-MS showed that the reaction was complete. The reaction was quenched with water (40 mL), and the reaction mixture was extracted with CH2Cl2 (30 mL×3). The combined organic phases were washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuum. The residue was purified by preparative TLC (CH2Cl2/MeOH=10:1) to afford the desired product (28.6 mg, 25% yield) as a white solid. LC-MS: m/z 394.2 [M+1]+. 1H NMR (400 MHz, CD3OD-d4): δ 7.60 (s, 1H), 7.29˜7.22 (m, 4H), 7.19˜7.17 (m, 1H), 3.95˜3.92 (m, 2H), 3.69˜3.58 (m, 2H), 3.52˜3.46 (m, 3H), 3.21 (m, 1H), 3.06˜3.04 (m, 1H), 2.91˜2.76 (m, 2H), 2.58˜2.56 (m, 1H), 2.16 (m, 1H), 1.89˜1.81 (m, 2H), 1.78 (m, 2H), 1.27 (d, J=6.8 Hz, 3H).

Provenance & Evidence