Bromotrimethylsilane → HCID 19993501, compound

Participants

Reaction Conditions

Reaction Steps

Bromotrimethylsilane (1.4 ml, 10.6 mmol) was added to a solution of 9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]adenine (200 mg, 0.52 mmol) in dichloromethane (8 ml) and stirred under nitrogen for 16 h at 20° C. The solvents were evaporated in vacuo, co-evaporating the residue with methanol and toluene. The residue was recrystallised from water-acetone 1:1, affording 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]adenine (130 mg, 76%) as a white solid m.p. 218°-221° C. λmax (H2O), 259 (ε13,500)nm; νmax (KBr) 3400, 1700 and 1620 cm-1 ; δH [(CD3)2SO] 3.59 (4H, m, CH2OCH2P), 3.95 (1H, m, CH,OH), 4.27 (1H, m, CH2ON), 4.39 (1H, m, CH2ON), 7.43 (2H, br.s, D2O exchangeable, NH2), 8.16 (1H, s, H-2/H-8), 8.39 (1H, s, H-2/H-8); m/z (FAB+ve Ion), 320 (MH+). Found: C, 33.79; H, 4.79; N, 22.00%; C9H14N5O6P requires C, 33.86; H, 4.42; N, 21.94%.

Provenance & Evidence