Bromotrimethylsilane → HCID 6474552, compound

Participants

Reaction Steps

A solution of (E)-9-[4-(diisopropoxyphosphoryl) -2(hydroxymethyl)but-3-enyloxy]adenine (0.25 g, 0.63 mmol) in anhydrous N,N-dimethylformamide (5 ml) under nitrogen was treated with trimethylsilylbromide (1.24 ml, 9.4 mmol) at 0° C. and the solution stirred for 18 h at room temperature. The solvent was removed in vacuo coevaporatng several times with methanol and toluene and the residue chromatographed on C18 reverse phase silica gel eluting with water to give (E)-9-(2-hydroxymethyl-4-phosphonobut-3-enyloxy) adenine as a solid (30 g, 17%); λmax (H2O) 260 nm (13711); υmax (KBr) 3434, 1717, 1690, 1653, 1640, 1472, and 1414 cm-1 ; δH [(CD3)2SO] 2.78 (1H, m, CH), 3.38 (3H, br.s, 3×OH, H2O), 3.60 (2H, m, CH2OH) , 4.48 (2H, m, CH2ON), 5.99 (1H, m, PCH=CH), 6.48 (1H, m, PCH=CH), 7.37 (2H, br.s, D2O exchangeable NH2), 8.14 (1H, s, H-2/H-8), 8.34 (1H, s, H-2/H-8) (Found: C, 36.50; H, 4.45; N, 20.49%. C10H14N5O5P.0.9H2O requires C, 36.24; H, 4.77; N, 21.13%).

Provenance & Evidence