Abstract
The reaction of 4-chloro-5-amino-6-(1,3-dihydroxy-2-propyl)aminopyrimidine with excess ethyl orthoformate gave a cyclic acetal, viz., 6-chloro-9-(2-ethoxy-1,3-dioxan-5-yl)purine, amination of which yielded 6-amino-9-(2-ethoxy-1,3-dioxan-5-yl)purine. The presence of two configurational isomers with a diaxial orientation of the purine ring and the ethoxy group in the trans isomer and an equatorial orientation of the ethoxy group in the cis isomer was established for these compounds by 1H and 13C NMR and IR spectroscopy. The three-dimensional structure of trans-6-chloro-9-(2-ethoxy-1,3-dioxan-5-yl)purine was determined by an x-ray difraction study, and the trans-diaxial orientation of the purine ring and the ethoxy group was confirmed; it is shown that the dioxane ring is in an anti conformation relative to the purine ring.
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M. Yu. Lidak, Ya. Ya. Shluke, B. V. Zarinya, and S. E. Poritere, Khim. Geterotsikl. Soedin., No. 2 262 (1971).
S. A. Giller, I. N. Goncharova, I. N. Getsova, L. N. Petrulyanis, L. I. Mironova, É. I. Bruk, and É. É. Liepin'sh, Khim. Geterotsikl. Soedin., No. 1, 132 (1975).
W. A. Szarek, D. M. Vyas, and B. Achmatowicz, J. Heterocycl. Chem., 12, 123 (1975).
E. E. Leuttzinger, W. A. Bowles, R. K. Robins, and L. B. Townsend, J. Am. Chem. Soc., 90, 127 (1968).
W. A. Bowles, F. H. Schneider, L. R. Lewis, and R. K. Robins, J. Med. Chem., 6, 471 (1963).
N. S. Zefirov and N. M. Shekhtman, Usp. Khim., 40, 593 (1971).
W. A. Szarek, D. M. Vyas, and B. Achmatowicz, Tetrahedron Lett., No. 19, 1553 (1975).
A. F. Mishnev, Ya. Ya. Bleidelis, I. N. Goncharova, and N. P. Ramzaeva, Izv. Akad. Nauk Latv. SSR, Ser. Khim. (1979, in press).
A. V. Bogatskii, Yu. Yu. Samitov, A. I. Gren', L. N. Vostrova, T. I. Davidenko, and Mamontov, Zh. Org. Khim., 10, 632 (1974).
E. L. Eliel and P. O. Hutchins, J. Am. Chem. Soc., 91, 2703 (1969).
A. J. Jones, E. L. Eliel, D. M. Grant, M. G. Knoeber, and W. F. Bailey, J. Am. Chem. Soc., 93, 4772 (1971).
Yu. Yu. Samitov, A. V. Bogatskii, A. I. Gren', A. V. Agatov, and V. N. Khudyakova, Zh. Org. Khim., 5, 1975 (1969).
D. G. Watson, R. M. Sweet, and R. E. Marsh, Acta Crystallogr., 19, 573 (1965).
R. F. Stewart and L. H. Jensen, J. Chem. Phys., 40, 2071 (1964).
P. J. Wheatly, Acta Crystallogr., 13, 80 (1960).
D. G. Watson, D. J. Sutor, and P. Tollin, Acta Crystallogr., 19, 111 (1965).
M. Ohki, A. Takenaka, H. Shimanouchi, and J. Sasada, Acta Crystallogr., B33, 2954 (1977).
M. Ohki, A. Takenaka, H. Shimanouchi, and J. Sasada, Acta Crystallogr., B33, 2956 (1977).
Y. Kobayashi and Y. Litaka, Acta Crystallogr., B33, 925 (1977).
F. W. Nader, Tetrahedron Lett., No. 14, 1207 (1975).
F. W. Nader, Tetrahedron Lett., No. 19, 1591 (1975).
E. L. Eliel and M. K. Kaloustian, Chem. Commun., No. 5, 290 (1970).
S. Wolfe, Acc. Chem. Res., 5, 102 (1972).
Yu. V. Zefirov and P. M. Zorkii, Zh. Struk. Khim., 15, 118 (1974).
Yu. V. Zefirov and P. M. Zorkii, Zh. Struk. Khim., 17, 994 (1976).
G. Germain, P. Main, and M. M. Woolfson, Acta Crystallogr., A27, 368 (1971).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 976–983, July, 1979.
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Mishnev, A.F., Bleidelis, Y.Y., Liepin'sh, É.É. et al. Synthesis and structure of 6-substituted 9-(2-ethoxy-1,3-dioxan-5-yl)purines. Chem Heterocycl Compd 15, 798–804 (1979). https://doi.org/10.1007/BF00473568
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DOI: https://doi.org/10.1007/BF00473568