Formic Acid → 9-(3-Hydroxypropoxy)guanine

Participants

Reaction Steps

9-(3-Benzyloxyprop-1-oxy)-6-chloro-2-formamidopurine (3.40 g, 9.41 mmol) in 80% formic acid (100 ml) was heated at 100° C. for 1 hour. The reaction mixture was then cooled and stirred with 10% palladium on charcoal (2.0 g) under an atmosphere of hydrogen at 20° C. for 45 minutes. After removal of the catalyst, the solution was evaporated and the residue was treated with water (50 ml) and concentrated aqueous ammonia (4 ml) at 100° C. for 15 minutes. The solution was then cooled and evaporated under reduced pressure. Recrystallisation of the residue from water afforded 9-(3-hydroxyprop-1-oxy)guanine (800 mg, 33%). 1H NMR: δH [(CD3)2SO] 1.80 (2H, quintet, J=6.3, 6.6 Hz, CH2CH2CH2), 3.55 (2H, quartet, J=5.50, 5.8 Hz, CH2OH), 4.32 (2H, t, J=6.6 Hz, CH2ON), 4.57 (1H, t, J=5.5 Hz, D2O exchangeable, OH), 6.57 (2H, br.s, D2O exchangeable, NH2), 7.91 (1H, s, H-8), 10.63 (1H, br.s, D2O exchangeable, H-1).

Provenance & Evidence