Abstract
2-Methylthio-4-hydroxypyrimidines react with methylbromoacetate in methanol-sodium methoxide solution to give O- and N(3)-alkylated products, namely, 2-methylthio-4-(methoxycarbonyl)methoxypyrimidines and 2-methylthio-3-(methoxy-carbonyl)methylpyrimid-4-ones.
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H. Wheeler and L. M. Liddle, J. Am. Chem. Soc., 30, 1152 (1908).
B. Agai, Gy. Hornyak, and K. Lempert, Period. Polytech. Chem. Eng., 18, 47 (1974); RZhKh, 18Zh333.
J. P. Jonak, G. C. Hopkins, H. J. Minnemeyer, and H. Tieckelmann, J. Org. Chem., 35, 2512 (1970).
L. N. Short and H. W. Thompson, J. Chem. Soc., No. 1, 168 (1952).
D. Shugar and J. J. Fox, Bull. Soc. Chim. Belg., 61, 293 (1952).
E. Wittenburg, Chem. Ber., 99, 2380 (1966).
D. J. Brown, E. Hoerger, and S. F. Mason, J. Chem. Soc., No. 1, 211 (1955).
J. J. Fox, N. Yung, and I. Wempen, Biochim. Biophys. Acta, 23, 295 (1957).
H. L. Wheeler and H. F. Merriam, Am. Chem. J., 29, 478 (1903).
I. B. Simon and I. I. Kovtunovskaya, Zh. Obshch. Khim., 21, 760 (1951).
R. S. Goody and R. T. Walker, J. Org. Chem., 36, 727 (1971).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1520–1522, November, 1987.
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Vainilavichyus, P.I., Syadyaryavichyute, V.Y. Alkylation of 2-methylthio-4-hydroxypyrimidines by methyl bromoacetate. Chem Heterocycl Compd 23, 1216–1218 (1987). https://doi.org/10.1007/BF00479372
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DOI: https://doi.org/10.1007/BF00479372