By Desmond J. Brown
Chapter I advent to the Pyrimidines (H 1, E 1) (pages 1–20):
Chapter II The vital man made process (H 31, E 20) (pages 21–62):
Chapter III different tools of basic 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 comparable Derivatives (H 389, E 296) (pages 367–404):
Chapter XII The diminished f'yrimidines (H 430. E 322; by means 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
2 )Hydroxy- to Mercaptopyrimidines ( H 16, E 8 ) (Ch. VII, Sect. B) Direct thiation of 2- or 4/6-hydroxypyrimidines with pure phosphorus pentasulfide in pyridine or a picoline is now widely applicable, although 2-hydroxypyrimidines are more resistant. The presence of an amino group no longer appears to be disadvantageous since the advent of pyridine in place of xylene or tetralin as the usual medium. 4842 Lawesson's reagent offers an excellent means to thiate 2-hydroxy- or 2 - 0 x o p y r i m i d i n e s .
B). D. 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.
Alkoxypyrimidines) by alkylation is dependent on position; 5- and extranuclear-hydroxypyrimidines undergo 0-alkylation by alkyl halide/ alkali or other regular alkylating procedures, but 2- and 4/6-hydroxypyrimidines usually need quite specialized procedures to give an appreciable proportion of 0-alkyl derivatives in the products, as discussed 18 in Ch. VII, Sect. D. In contrast, 0-acylation to give, for example, 4acetoxy-5-butyl-2-dimethylamino-6-methylpyrimidine(62), usually proceeds quite normally in acetic anhydride or the like, whatever the position of the hydroxy group (Ch.