Bromotrimethylsilane → (S)-9-[3-Hydroxy-2-(phosphonomethoxy)propoxy]guanine

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To a solution of (S)-2-amino-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-methoxypurine (0.56 g, 1.38 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.82 ml, 13.8 mmol) and the solution stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue co-evaporated with acetone/water 1:1 (x2). The white solid obtained was crystallised from hot water to give the title compound as a white solid (0.305 g, 66%). IR:νmax (KBr) 3380, 3320, 3160, 1715, 1645, 1600, 1385, 1185, 1160, 1100, 1060, 1045, 925, 770 cm-1. 1H NMR: δH (D2O+NH3) 3.61 (1H, dd, J=12.1 Hz J=9.9 Hz, CHBP), 3.65-3.75 (2H, m, CHAP, CHBOH), 3.82-3.89 (1H, m, CH), 3.93 (1H, dd, J=12.3 Hz, J=3.6 Hz, CHAOH), 4.46-4.53 (2H, m, NOCH2), 8.03 (1H, s, H-8). Found: C, 32.24; H, 4.16; N, 20.59%. C9H14N5O7P requires: C, 32.24; H, 4.21; N, 20.89%. m/z: (FAB, thioglycerol matrix) 336 (MH+). [α]D25 (0.1M NaOH)+12.8° (c=0.43).

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