反应详情

A solution of trimethylsilylated guanine in benzene (25 ml) prepared as in Example 6 (from 2.0 g of guanine) containing triethylamine was heated at reflux and 3-benzoyloxy-propoxymethyl chloride (2.96 g) dissolved in benzene (15 ml) was added over a 3 hour period. The reaction mixture was heated at reflux under nitrogen overnight. The solvent was removed under reduced pressure, and 95% ethanol and methanol were added to the residual oil. The mixture was heated on a steam bath for several minutes and the solvent then evaporated under reduced pressure. Chloroform (200 ml) was added and the resulting solid removed by filtration. The solid was dissolved in a minimal amount of DMF, filtered (to remove any guanine present) and reprecipitated by the addition of water. Recrystallization from methanol (with charcoaling) gave 9-(3-benzoyloxypropoxymethyl)guanine (0.94 g) as a pale yellow solid, m.p. 198°-201° C.

1. temperaturewas heated
2. temperatureat reflux
3. additionwas added over a 3 hour period
4. temperatureThe reaction mixture was heated
5. temperatureat reflux under nitrogen overnight
6. customThe solvent was removed under reduced pressure, and 95% ethanol and methanol
7. additionwere added to the residual oil
8. temperatureThe mixture was heated on a steam bath for several minutes
9. customthe solvent then evaporated under reduced pressure
10. additionChloroform (200 ml) was added
11. customthe resulting solid removed by filtration
12. dissolutionThe solid was dissolved in a minimal amount of DMF
13. filtrationfiltered (
14. customto remove any guanine present) and
15. customreprecipitated by the addition of water
16. customRecrystallization from methanol (with charcoaling)