Allyl bromide → HCID 9994808, compound

Participants

Reaction Steps

To a solution of 2-amino-6-chloro-9-(4-hydroxybutyl)-8-oxo-7H-purine (0.8 g, 3.1 mM) in DMF (15 mL) was added NaH (0.12 g, 60% oil dispersion, 3 mM) all at once at zero degrees C. under nitrogen and stirred for 30 minutes. To this was added allyl bromide (0.37 g, 3.1 mM) and the resulting mixture was allowed to warm to room temperature and stirred overnight. Most of solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (120 g, CH2Cl2 /CH3OH/conc. NH4OH, 100/5/0.1) to give 7-allyl-2-amino-6-chloro-9-(4-hydroxybutyl)-8-oxo-7H-purine as an off-white powder (40 percent) mp 132°-133° C. IR (KBr) 3320, 1715, 1640, 1585, 1460 cm-1. 1H NMR (DMSO-d6) δ 6.70 (bs, 2H, exchangeable, NH2), 5.95 (m, 1H), 3.70 (t:, J=6.5 Hz, 2H, NCH2), 3.35 (m, 2H, CH2OH), 1.50 (m, 4H, CH2CH2).

Provenance & Evidence