By Desmond J. Brown
Chapter I creation to the Pyrimidines (H 1, E 1) (pages 1–20):
Chapter II The relevant artificial strategy (H 31, E 20) (pages 21–62):
Chapter III different equipment 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 one hundred 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 lowered f'yrimidines (H 430. E 322; via 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
5382 The Principal Synthetic Method Ye Me 31 7F3 Me Substituted guanidines have been condensed extensively with P-diketones. Thus, ethyl guanidine and acetylacetone gave 2-ethylamino4,6-dimethyIpyrimidine (62);4551although the yield was poor, this was probably not due to the alternative formation of the strongly basic isomer (63), which would have undoubtedly undergone Dimroth rearrangement to the ethylaminopyrimidine (62) under the reaction conditions. 6205 Similarly, phenylbiguanides (66) gave 4,6-dimethyl-2-Nfphenylguanidinopyrimidine (67) and related c o m p o ~ n d s .
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. VII, Sect. 6373 16 Chapter I G. Reductive Reactions (H21, E 13) ( 1) Nuclear Reduction ( H 2 1, E 13) The relatively small amount of material on nuclear reduction of pyrimidines is covered in Ch.
5590 However, 29 The Principal Synthetic Method acetylacetone did condense with 4-cyano-2-ethoxycarbonylbutyramidine in ethanol containing piperidine to give 2-(y-cyano-cu-ethoxycarbonylpropyl)-4,6-dimethylpyrimidine (46) in reasonable yield. 5098 Much better results were obtained using the acylketene thioacetals as diketone equivalents. Thus, 2-benzoyl-3,3-bisniethylthioacrylonitrile (47, R = SMe) and acetamidine in refluxing dimethylformamide containing triethylamine gave 5 -cyano-2-methyl-4-methylthio-6-phenylpyrimidine (48, R = Me) in 90% yield.
Chemistry of Heterocyclic Compounds: The Pyrimidines: Supplement II, Volume 16 by Desmond J. Brown