Collect. Czech. Chem. Commun. 1994, 59, 1853-1869

Preparation of 9-(2-Phosphonomethoxyethyl)adenine Esters as Potential Prodrugs

Petr Alexander, Antonín Holý and Milena Masojídková

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Esters of 9-(2-phosphonomethoxyethyl)adenine with substituted aliphatic alcohols were prepared as potential prodrugs. Activation of the phosphonate moiety with dimethylchloromethyleneammonium chloride, generated by reaction of thionyl chloride or triphosgene with dimethylformamide, proved to be the method of choice. The esters were also prepared by alkylation of the phosphonate group with dimethylformamide dialkyl acetals or a mixture of the appropriate alcohol with dimethylformamide dineopentylacetal.