Hydrochloric Acid → 9-(3,4-dihydroxybutyl)guanine

Participants

Reaction Steps

To a suspension of ethyl 4-(2-amino-1,6-dihydro-6-oxopurin-9-yl)-2-hydroxybutyrate (prepared according to Example 4) in iso-propanol was added an excess of sodium borohydride and the mixture was refluxed over night (at least 8 hours). Hydrochloric acid was added until a clear solution was obtained (neutral pH). After removal of the solvent the residue was dissolved in a minimum amount of boiling water and kept at 0° C. for a couple of hours. The solid was filtered off. The filtrate was evaporated at reduced pressure and the residue dissolved in hydrochloric acid (1 mol/l) and adsorbed on a cation exchange resin (Dowex 50 W, H+ -form). The resin was washed with water and then eluted with 5% ammonium hydroxide. The eluent was evaporated to give a crystalline solid which was recrystallized from water to afford colourless needles. M.p. 260°-1° C. (dec.) (uncorrected) UV spectra (hydrochloric acid 0.01 mol/l): λmax (nm) 277, 253 (ε=11500) M.S: 11.2 a J. (int): 239 (M+, 0.13), 222 (0.19), 221 (0.11), 152 (0.43), 151 (0.56), 44 (1.0).

Provenance & Evidence