Bromotrimethylsilane → 9-[1-Hydroxy-4-(phosphonomethoxy)but-2-oxy]guanine

Participants

Reaction Conditions

Reaction Steps

A solution of 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine (95 mg, 0.23 mmol) in N,N-dimethylformamide (5 ml) was treated with bromotrimethylsilane (0.62 ml, 4.6 mmol) and stirred at 20° C. for 3 h. The reaction mixture was evaporated in vacuo, the residue dissolved in water and passed down reverse- phase silica eluting with water. Evaporation of the appropriate fractions in vacuo gave a white foamy solid which was recrystallised from acetone-water, affording 9-[1-hydroxy-4-(phosphonomethoxy)but-2-oxy]guanine (20 mg, 24%) as a white solid m.p. 188°-192° C. νmax (KBr) 3400, 3100, 1700, 1650 and 1600 cm-1 ; δH [(CD3)2SO] 1.85 (2H, m, HOCH2CHCH2), 3.30 (2H, br.s, D2O exchangeable, P(OH)2), 3.4-3.7 (6H,m, CH2OCH2P+CH2OH), 4.30 (1H, m, HOCH2CH), 5.0 (1H, br.s, D2O exchangeable, OH), 6.62 (2H, br.s, D2O exchangeable, NH2), 7.86 (1H, s, H-8); m/z (FAB+ve Ion), 372 (MNa+), 350 (MH+); Found: C, 33.97; H, 4.69; N, 20.11%; C10H16N5O7P requires C, 34.29; H, 4.62; N, 20.10%.

Provenance & Evidence