Displacement of di-and trichloropyrimidines with potassium fluoride in
-N, N-dimethylformamide under milder conditions afforded corresponding fluoropyrimidine derivatives in good yields, wherein the reaction products were, in most cases, separated from solvents by steam distillation. The di-and trifluoropyrimidines were further treated with alcoholic ammonia to yield amino-fluoro compounds, and with sodium benzyloxide followed by reduction over palladium carbon to yield hydroxy-fluoro compounds. Comparison of ultraviolet absorption spectra of the fluoropyrimidine derivatives with those of corresponding chloro compounds revealed that conversion of substituent from chlorine to fluorine shifted the absorption bands about 10∼20 mμ toward blue. The derivatives of pyrimidine (Py) newly described are as follows : 2, 4, 6-trifluoro-5-methyl-Py (IIb), 2, 4-difluoro-5, 6-dimethyl-Py (IId), 4, 6-difluoro-2-methyl-Py (IIe), 4, 6-difluoro-2, 5-dimethyl-Py (IIf), 4, 6-difluoro-5-methyl-Py (IIg), 4-amino-2, 6-difluoro-5-methyl-Py (IIIb), 4-amino-2-fluoro-6-methyl-Py (IIIc), 4-amino-2-fluoro-5, 6-dimethyl-Py (IIId), 4-amino-6-fluoro-2-methyl-Py (IIIe), 4-amino-6-fluoro-2, 5-dimethyl-Py (IIIf), 4-amino-6-fluoro-5-methyl-Py (IIIg), 2-amino-4, 6-difluoro-5-methyl-Py (IVb), 2-amino-4-fluoro-6-methyl-Py (IVc), 4-benzyloxy-6-fluoro-2-methyl-Py (Ve), 4-benzyloxy-6-fluoro-2, 5-dimethyl-Py (Vf), 4-benzyloxy-6-fluoro-5-methyl-Py (Vg), 4-fluoro-6-hydroxy-2-methyl-Py (VIe), 4-fluoro-6-hydroxy-2, 5-dimethyl-Py (VIf), and 4-fluoro-6-hydroxy-5-methyl-Py (VIg).
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