Purines. LX. Dimroth Rearrangement and Concomitant Hydrolytic Deamination of 7-Alkyl-1-methyladenines

Abstract

The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7-alkyl-N⁶-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methylhypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H₂O for 4-70 h. Probable pathways leading to these by-products are proposed.