Bromotrimethylsilane → [(Z)-4-(6-aminopurin-9-yl)oxybut-1-enyl]phosphonic acid

Participants

Reaction Steps

To a solution of (Z)-9-[4-(diethoxyphosphoryl)-but-3-enyloxy]adenine (145 mg, 425 μmol) in dichlormethane (10 ml) was added bromotrimethylsilane (1.29 g, 8.48 mmol) and the resulting solution was stirred at room temperature under dry nitrogen for 18 hr. The solvent was removed and the residue was azeotroped with methanol (×5). The residue was purified by column chromatography on reverse phase silica gel eluting with water to give (Z)-9-(4-phosphonobut-3-enyloxy]adenine as a white solid (98 mg, 81%), m.p. 238° C.; λmax (MeOH) 260 (13,515)nm; υmax (KBr) 3420, 3200, 3085, 2970, 1700, 1610, 1485, 1415 and 1335 cm-1 ; δH [(CD3)2SO] 2.94 (2H, m, CH2), 4.43 (2H, t, J 7 Hz, CH2O ), 5.77 (1H, dd, J 14 Hz and 17 Hz, PCH=CH), 6.40 (1H, ddt, J 7 Hz, 14 Hz and 47 Hz, PCH=CH), 7.40 (2H, br.s, NH2). 8.15 (1H, s, H-2/H-8), 8.42 (1H, s, H-2/H-8); FABMS (thioglycerol) 286 (NH+) (Found: C, 36.71; H, 4.16; N, 23.96%. C9H12N5O4P.0.4H20 requires C, 36.96; H, 4.41; N, 23.95%).

Provenance & Evidence