Hydrochloric Acid → 7-(2-Hydroxyethyl)adenine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 16 (0.207 g, 0.999 mmol) and water (0.50 mL) in THF (12 mL) was added NaBH4 (0.38 g, 10.0 mmol). After stirring for 4 h at 25° C., the reaction mixture was neutralized to pH=7.0 by use of 10% HCl aqueous solution. Solvent was evaporated under reduced pressure and the residue was purified by column chromatography (EtOAc/hexanes=9:1) to give 18 (0.10 g, 0.55 mmol) in 55% yield: mp 132-133° C.; Rf(hexanes/EtOAc=1:2) 0.09; UV (EtOH) λmax 265 (ε 14,110); 1H NMR (CD3OD) δ 3.68 (t, J=5.9 Hz, 2 H, CH2O), 3.66 (t, J=5.9 Hz, 2 H, CH2N), 8.34 (s, 1 H, HC2), 8.68 (s, 1 H, HC8); MS m/z 179 (M+). Anal (C7H9N5O) C, H, N; calcd (%): 46.92, 5.06, 39.08; found (%): 47.01, 5.12, 39.11.

Provenance & Evidence