Bromotrimethylsilane → 2,6-Diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine (100 mg, 0.26 mmol) in dichloromethane, was added bromotrimethylsilane (0.34 ml, 2.6 mmol) and the solution stirred under nitrogen for 4 h at 20° C. The solution was evaporated in vacuo and co-distilled with methanol and toluene. Recrystallisation of the residue with ethanol-water afforded 2,6-diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine (55 mg, 65%) as a white solid m.p. >300° C. decomp. λmax (H2O), 280 (ε10,100), 255 (ε8,400), 212 (ε26,100); νmax (KBr) 3360, 1700, 1660 and 1410 cm-1 ; δH (D2O+NH3) 3.55 (2H, m, CH2OH), 3.89 (4H, m, CH2OCH2P), 4.62 (1H, m, CHON), 8.10 (1 H, s, H-8). Found: C, 32.49; H, 4.63; N, 24.86%; C9H15N6O6P requires C, 32.34; H, 4.52; N, 25.14%.

Provenance & Evidence