Alkaline degradation of 1,3-Di-(2-Hydroxyethyl)adenosine 3′,5′-cyclic phosphate. Studies on the reaction products

Abstract 1,3-Di-(2-hydroxyethyl)adenosine 3′,5′-cyclic phosphate (1) in 1 M NaOH failed to undergo the expected Dirmroth rearrangement. Rather, pyrimidine ring opening followed by loss of ethylene oxide and formate yielded 5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-(2-hydroxyethyl)-carboxamidine) 3′,5′-cyclic phosphate (2) as the major product. The 3′-monophosphate (3) and 2′-O-hydroxyethyl (4) derivatives of 2 were also isolated and characterized.