Collect. Czech. Chem. Commun. 1983, 48, 1910-1921

Preparation of isomeric 3-aminopropylamino derivatives of 9-(RS)-(2,3-dihydroxypropyl)adenine

Antonín Holý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Treatment of 9-(RS)-(2,3-dihydroxypropyl)adenine (III) with bromine in water afforded the 8-bromo derivative IV which on reaction with acetone was converted into the 1,3-dioxolane derivative VI. Reaction of compound VI with 1,3-diaminopropane, followed by acid hydrolysis, gave 9-(RS)-(2,3-dihydroxypropyl)-8-(3-aminopropylamino)adenine (VIII). Compound IV reacts with 1,3-diaminopropane under formation of a mixture of compound VIII and isomeric 9-(RS)-[3(2)-(3-aminopropylamino)-2(3)-hydroxypropyl]-8-hydroxyadenines (IX, X). 9-(RS)-(2,3-Dihydroxypropyl)-8-hydroxyadenine (XVII) was prepared by reaction of compound VI with sodium benzoxide in dimethylformamide and subsequent acid hydrolysis. Its tosylation, followed by reaction of the obtained 3'-O-p-toluenesulfonyl derivative XVIII with 1,3-diaminopropane, furnished also the compound IX. In an analogous way, 9-(RS)-[3-(3-aminopropylamino)-2-hydroxypropyl]adenine (XXI) was prepared from 3'-O-p-toluenesulfonyl derivative of compound III (XX).