Bromotrimethylsilane → HCID 136051123, compound

Participants

Reaction Steps

To a solution of 9-[3-(diethoxyphosphoryl)propoxy]guanine (110 mg, 0.32 mmol) in dry DMF (2 ml) was added bromotrimethylsilane (0.25 ml, 1.91 mmol). The solution was left at ambient temperature for 24 hours, evaporated to dryness under reduced pressure, the residue dissolved in methanol and the solution evaporated to dryness again. The resulting solid was washed again with methanol. The solid was suspended in water (2 ml) and 0.880 NH3 added to obtain a solution. The solution was passed through a column of Dowex 50W-X8(H) ion-exchange resin (previously washed with water) and the column eluted with water. The UV absorbing fractions were collected and evaporated to dryness to give the title compound as a white solid (45 mg, 50%), m.p. >300° C. UV: λmax (EtOH) 255 mm. IR: υmax (KBr) 3700-2100 (broad), 1743, 1700, 1662, 1552, 1474, 1419, 1327, 1240, 1164, 1080, 1029, 1011, 969, 775, 694 cm-1 . 1H NMR: δH ((CD3)2SO) 1.6-1.9 (4H, m, CH2CH2P), 4.28 (2H, t, J=7 Hz, O--CH2), 6.59 (2H, bs, D2O exchangeable, NH2), 7.92 (1H, s, H-8), 10.63 (1H, bs, D2O exchangeable, NH), 2.5-4.5 (2H, broad, D2O exchangeable, PO(OH)2). C8H12N5O5P. 0.75 H2O requires C, 31.74; H, 4.34; N, 23.14%. Found: C, 31.96; H, 4.13; N, 23.01%.

Provenance & Evidence