Abstract
The reaction of 2, 4, 5-triamino-6-hydroxypyrimidine with phosphorus pentasulfide in quinoline has yielded 2, 4, 5-triamino-6-mercaptopyrimidine. 8-Hydroxymethyl derivatives of guanine and thioguanine have been synthesized by the acylation of 2, 4, 5-triamino-6-hydroxypyrimidine and the corresponding 6-mercapto compound with glycolic acid or ethyl glycolate, with subsequent treatment of the resulting 5-hydroxyacetylamino derivatives with aqueous alkali.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. F. Larionov, The Chemotherapy of Malignant Tumors [in Russian], Gosmedizdat, Moscow, pp. 178, 183, 1962.
W. Traube, Ber., 33, 1371, 1900.
V. M. Berezovskii and L. I. Strel'chunas, Tr. VNII vitaminov, 5, 128, 1954.
G. B. Elion, W. H. Lange, and G. H. Hitchings, J. Am. Chem. Soc., 78, 2858, 1956.
J. Mervin, J. Med. Chem., 7, 792, 1964.
G. Levin, A. Kalmus, and F. Bergmann, J. Org. Chem., 25, 1752, 1960.
G. H. Hitchings and G. B. Elion, J. Am. Chem. Soc., 71, 467, 1949.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Studentsov, E.P., Nemets, V.G. Synthesis of 8-hydroxymethyl derivatives of guanine and thioguanine. Chem Heterocycl Compd 4, 538–539 (1971). https://doi.org/10.1007/BF00486782
Issue Date:
DOI: https://doi.org/10.1007/BF00486782