Synthesis of 2-Amino-5-(3-chloropropyl)-4-chloro-7Hpyrrolo[2,3-d]pyrimidine (Bischlorinated Deazaguanine)

摘要

There are many forms of DNA damage which may arise from the modifications DNA bases. Deazaguanine is a modified DNA base which is recognised by DNA repair enzyme, Methylguanine DNA-methyltranferase (MGMT). The synthesis of bischlorinated deazaguanine was successfully carried out via two different routes. The first route was achieved through the reaction of pyrrolopyrimidine with benzyl(triethyl)ammonium chloride, dry dimethylaniline and freshly distilled phosphoryl chloride in acetonitrile under argon atmosphere. An alternative method was employed toward achieving the bischolorinated through the debenzoylation of the protected pyrrolopyrimidine with 1 M NaOH at 50℃ for 1h followed by double chlorination reaction using phosphoryl chloride alone at 80℃ for 1h. Both routes were found to be successful with lower impurities recorded from the second route though it gives a low yield but it was shorter.