Ethyl bromoacetate → 9H-Purine-9-acetic acid, 6-(benzoylamino)-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

Compound 8 (2.39 g, 10 mmol) was dissolved in dry DMF (100 mL), cooled to 0° C., sodium hydride (0.48 g, 20 mmol) was added, and the mixture stirred at room temperature for 30 min. Ethyl bromoacetate (1.22 mL, 11 mmol) was added dropwise for 1 h. Stirring was continued for 2 h at room temperature and the reaction was quenched with methanol (2 mL). The solvents were evaporated under reduced pressure. The residue was subjected to column chromatography (DCM/MeOH; 9.5/0.5) to obtain 9 as a white solid: yield 1.3 g (40%); MS(+ESI): m/z 326 [M+H]+; 1H NMR (400 MHz, CDCl3): δ9.02 (s, 1H), 8.83 (s, 1H), 8.11 (s, 1H), 8.05 (d, 2H, J=7.2 Hz), 7.62 (t, 1H, J=7.2 Hz), 7.54 (t, 2H, J=7.2 Hz), 5.06 (s, 2H), 4.31 (q, 2H, J=7.2 Hz), 1.38 (t, 3H, J=7.2 Hz); 13C NMR (400 MHz, CDCl3): δ=166.76, 164.53, 152.96, 152.50, 149.83, 143.22, 133.68, 132.80, 128.89, 127.85, 122.56, 62.53, 44.33, 14.09.

Provenance & Evidence