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Communication | Special issue | Vol 5, No. 1, 1976, pp.255-260
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0255
1,3-Dipolar Cycloaddition of 4-Alkoxy-6-methylpyrimidine N-Oxides

Hiroshi Yamanaka,* Setsuko Niitsuma, Takao Sakamoto, and Michinao Mizugaki

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

While 1,3-dipolar cycloaddition of 4-ethoxy-6-methylpyrimidine N-oxide (Ia) with phenyl isocyanate gave the expected product, 2-anilino-4-ethoxy-6-methylpyrimidine (II), the reaction of Ia with phenyl isothiocyanate afforded 3-phenyl-7-methyl-2,3-dihydro-oxazolo[4,5-d]pyrimidine-2-thione (IV).
The reaction of 4-alkoxy-6-methylpyrimidine N-oxides (I) with dimethyl acetylenedicarboxylate afforded methyl 4-alkoxy-6-methyl-2-pyrimidineacetates (IX).