Bromotrimethylsilane → HCID 19808624, compound

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Reaction Steps

A solution of 9-[2-hydroxy-4-(diethoxyphosphoryl)butoxy]adenine (0.50 g, 0.14 mmol) and bromotrimethylsilane (0.184 ml, 1.4 mmol) in dry dimethylformamide (3 ml) was stirred at room temperature for 3 hours. The solvent was then evaporated and the residue was coevaporated with dimethylformamide (2×5 ml) and methanol:water (9:1) solution. The product crystallised from water:methanol (9:1) solution to give the title compound (35 mg, 83%); m.p. 265°-267° C. 1H NMR: δH [(CD3)2SO] 1.6 (4H, m, CH3CH2CH2P), 3.8 (1H, m, CHCH2CH2P) 4.25 (2H, m, OCH2) 7.41 (2H, br. s, D2O exchangeable, NH2), 8.16 (1H, s, H-2), 8.36 (1H, s, H-8). Found: C, 35.78; H, 4.52; N, 22.25%. C9H17N5PO5 requires: C, 35.65; H, 4.65; N, 23.1%.

Provenance & Evidence