Bromotrimethylsilane → 2-Amino-6-chloro-9-[2-(phosphonomethoxy)ethoxy]purine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.370 g, 0.91 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.3 ml, 9.6 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 (×2). The solid residue obtained was crystallised from hot water to give the title compound as a tan solid (0.15 g, 51%), m.p. 190°-195° C. IR: νmax (KBr) 3480, 3430, 3200, 3150, 2920, 1660, 1625, 1570, 1525, 1480, 1370, 1320, 1235, 1195, 1125, 1105, 1030, 995, 950, 920, 880, 780 cm-1. 1H NMR: δH [(CD3)2SO] 3.63 (2H, d, J=8.52 Hz, OCH2P), 3.81 (2H, m, CH2OCH2P), 4.45 (2H, m, N-OCH2), 2.75-5.25 (2H, broad, D2O exchangeable PO(OH)2), 7.11 (2H, br.s, D2O exchangeable NH2), 8.37 (1H, s, H-8). Found: C,28.89; H,3.51; N,21.15%. C8H11N5O5PCl. 0.5H2O requires: C,28.88; H,3.63; N,21.06%.

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