Bromotrimethylsilane → HCID 19819549, compound

Participants

Reaction Steps

A solution of 9-[3-hydroxy-2-(diethoxyphosphorylmethylthio)propoxy]adenine (0.265 g, 0.67 mmol) in dry dichloromethane (20 ml) was treated with bromotrimethylsilane (1.53 g, 10 mmol) at room temperature and allowed to stand for 6 hours. The solvent was removed under reduced pressure and the residue was dissolved in methanol, before being allowed to stand for 5 minutes. The solution was evaporated to dryness under reduced pressure, re-dissolved in methanol, neutralized with AMBERLITE IR 45 OH resin and filtered and evaporated in vacuo. The residue was crystallised from water to give the title compound (180mg, 80%) as colourless crystals, m.p. 195°-97° C. λmax (H 2 O) 260nm (ε 14,000) υmax (KBr) 3320, 3110, 2920, 1720, 1595, 1550, 1490, 1460, 1405, 1340 and 1300 cm-1 ; δH [(CD3)2SO] 2.70 (2H,d, J 13.5Hz, PCH2S), 3.3 (1 H, m, CH), 3.7 (1H, m, CH ofCH2OH), 3.8 (1H, m, CH of CH2OH), 4.6 (2H, m, CH2O), 7.6 (2H, br s, exchangeable with D2O, NH2), 8.2 (1H, s, 2-H), 8.46 (1H, s, 8-H).

Provenance & Evidence