By Desmond J. Brown
Chapter I advent to the Pyrimidines (H 1, E 1) (pages 1–20):
Chapter II The relevant man made procedure (H 31, E 20) (pages 21–62):
Chapter III different tools of fundamental Synthesis (H eighty two, E fifty three) (pages 63–108):
Chapter IV Pyrimidine and its C?Alkyl and C?Aryl Derivatives (H 116, e86) (pages 109–134):
Chapter V Nitro Nitroso and Arylazopyrimidines (H 138, b ninety four) (pages 135–156):
Chapter VI Halogenopyrimidines (H 162, E a hundred and ten) (pages 157–224):
Chapter VII Hydroxy? and Alkoxypyrimidines (H 227, E 166) (pages 225–268):
Chapter VIII Sulfur?Containing Pyrimidines (H 272, E 202) (pages 269–298):
Chapter IX The Aminopyrimidines (H 306, E 230) (pages 299–328):
Chapter X The N?Alkylated Pyrimidines and the Pyrimidine N?Oxides (H 356, E 269) (pages 329–366):
Chapter XI The Pyrimidine Carboxylic Acids and similar Derivatives (H 389, E 296) (pages 367–404):
Chapter XII The decreased f'yrimidines (H 430. E 322; by way of R. F. Evans) (pages 405–478):
Chapter XIII The Ionization and Spectra of Pyrimidines (H 464, E 368) (pages 479–518):
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Additional resources for Chemistry of Heterocyclic Compounds: The Pyrimidines: Supplement II, Volume 16
VI, Sect. 5393 ( 8 ) Interchange o f Halogen Substituents (E 10) (Ch. VI, Sects. E and F) All 2- or 4/64odopyrimidines are still made only from their chloro or bromo analogues. 4526 (9) Hydroxy- to Aminopyrimidines (New) (Ch. VII, Sect. E) The conversion of hydroxy- into aminopyrimidines is usually done via a derived chloro-, alkylthio-, or alkoxypyrimidine. However, the semi-direct aminolysis of hydroxypyrimidines is now possible, providing 12 Chapter I OMe OSiMe, I I NHR I NH R I NH the substrate and product can withstand the required conditions.
Oxidative Reactions (H 20, E 13) The oxidation of nitroso- to nitropyrimidines (Ch. V, Sect. 6293 The useful oxidation of mercapto- to sulphopyrimidines is mentioned in Sect. A(4) above. Oxidation of alkylthio- to alkylsulfonylpyrimidines (usually by peroxy acids) is even more useful because it converts a sluggish into an excellent leaving group for nucleophilic displacements (Ch. C). ) is covered in Ch. IV, Sect. c. The introduction of a 5-hydroxy group by the Elbs persulfate oxidation has been studied again after many years of neglect (Ch.
Other Metatheses (H 16, E 7) (1) Hydroxy- to Chloropyrimidines ( H 16, E 7) (Ch. VI, Sect. ~ phoryl chloride, if necessary with the addition of N,N-diethylaniline in molar or submolar ratio to the substrate. 6377 Although the presence of amino groups is no longer considered any bar to the use of phosphoryl chloride, some other groups can be affected. For example, 5-acetyl-2,4-dihydroxypyrimidinegave 2,4-dichloro-5- 9 Introduction to the Pyrimidines (32) (33) OH c1- HZNOCHZC NMea (36) "'3. ~~~~?