Bromotrimethylsilane → 9-(4-Phosphonobutoxy)guanine
Reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2)([O:6]CC)=[O:5])C.Br[Si](C)(C)C>CN(C)C=O>[P:4]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:19](=[O:23])[NH:18][C:17]([NH2:24])=[N:16][C:15]1=2)([OH:5])([OH:6])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
9-[4-(Diethoxyphosphoryl)butoxy]guanine (0.12 g, 0.33 mmol) and bromotrimethylsilane (0.43 ml, 3.3 mmol) were dissolved in dimethylformamide (5 ml) and the reaction mixture was stirred at 23° C. for 3 hr. The solvent was evaporated under vacuum and the residue dissolved in methanol:water solution (9:1). The pH of the resulting solution was adjusted to 7.0 with diluted aq. ammonia and the solvents were evaporated to dryness. The product was purified by reversed phase chromatography (eluted with water) to give the title compound (65 mg, 64%) m.p. 208° C. (water), as its ammonium salt. 1H NMR: δH ((CD3)2, SO+D2O) 1.40 (2H, m, CH2P), 1.68 (4H, br.s, CH2CH2), 4.21 (2H, m, NOCH2), 7.89 (1H, s, H-8).