Triethylamine → 9-(2-Azidoacetoxyethoxy-methyl)guanine

Participants

Reaction Conditions

Reaction Steps

A solution of 0.84 ml (8.4 mmol) azidoacetyl chloride in 5 ml dry dimethylformamide was added dropwise over 10 minutes in an ice-cooled, thoroughly stirred suspension of 1.25 g (5.55 mmol) 9-(2-hydroxyethoxymethyl)guanine and 0.78 ml (5.55 mmol) triethylamine in 40 ml dry dimethylformamide. After 45 minutes of thorough stirring at 0° C., 0.11 ml (1.1 mmol) azidoacetylchloride in 1 ml dimethylformamide was added, and stirring was continued for 15 minutes. The reaction was stopped by the addition of 15 ml 7% NaHCO3 solution whereupon the mixture was evaporated to dryness in vacuo. The residue was triturated with 20 ml of a mixture of methylene chloride:diethyl ether:ethanol (volume ratio 5:5:1). The solid substance obtained was filtered off, thoroughly washed with cold water and recrystallised from hot water, after treatment with active carbon. 1.02 g (62%) of 9-(2-azidoacetoxyethoxy-methyl)guanine m.p. 175°-177° C. (decomposition) was obtained. MS m/e 308 (M30), 151 (base+H); IR (KBr) 2110 (N3), 1745 (COOR) cm-1 ; UV (phosphate buffer, pH=7) λmax 253 nm (ε 8.42× 103), 270 (sh); TLC Rf 0.27 (CHCl3 --MeOH, 8:2), Rf 0.60 (EtOH--HOAc, 8:2).

Provenance & Evidence