By Desmond J. Brown
Chapter I advent to the Pyrimidines (pages 1–30):
Chapter II The important artificial strategy (pages 31–81):
Chapter III different tools of basic Synthesis (pages 82–115):
Chapter IV Pyrimidine and its C?Alkyl and C?Aryl Derivatives (pages 116–137):
Chapter V Nitro?, Nitroso?, and Arylazo?Pyrimidines (pages 138–161):
Chapter VI Halogenopyrimidines (pages 162–226):
Chapter VII Hydroxy? and Alkoxy?Pyrimidines (pages 227–271):
Chapter VIII Sulphur?Containing Pyrimidines (pages 272–305):
Chapter IX The Aminopyrimidines (pages 306–355):
Chapter X The N,?Alkylated Pyrimidines and Pyrimidine?N,?Oxides (pages 356–388):
Chapter XI The Pyrimidine Carboxylic Acids and similar Derivatives (pages 389–429):
Chapter XII The decreased Pyrimidines (pages 430–463):
Chapter XIII The Ionization and Absorption Spectra of Pyrimidines (pages 464–500):
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Additional info for Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume 16
M 'These and similar formulae could of course be written in alternative tautomeric forms.
D). Almost all 2-, 4-,and 6-chloropyrimidines are readily replaced by a methoxy group with the help of methanolic sodium methoxide. g. of the 4-chlorine of (XXX}) tures above the boiling point of methanol ever used. Other allcoxides and aryloxides behave similarly. Chapter I I4 The need for completely anhydrous alcohols for use in such reactions, is underlined by the formation of 2-ethoxy-4-hydroxy-5nitropyrimidine (and its isomer) to the extent permitted by the water content of the “absolute alcohol” used in preparing 2,4-diethoxy-5nitropyrimidine from its dichloro analogue.
29. , London, 1950, 4th Edition, vol. 10, p. 137. 30. Brown, Revs. Pure and Appl. Chem. (Australia), 3, 115 (1953). 31. Wiley, in “Organic Chemistry” (Ed. Gilman), Wiley & Sons, New York, 1953, 2nd Edition, Vol. 4, p. 864. 32. Bendich, in “The Nucleic Acids” (Ed. Chargeff and Davidson), Academic Press,New York, 1955, Vol. 1, p. 81. 33. Kenner and Todd, in “Heterocyclic Compounds” (Ed. ElderfteId), Wiley I% Sons, New York, 1957, vol. 6, p. 234. 34. Ramage and Landquist, in “Chemistry of Carbon Compounds” (Ed.
Chemistry of Heterocyclic Compounds: The Pyrimidines, Volume 16 by Desmond J. Brown