By Desmond J. Brown
Chapter I creation to the Pyrimidines (H 1, E 1) (pages 1–20):
Chapter II The valuable 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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Extra resources for Chemistry of Heterocyclic Compounds: The Pyrimidines: Supplement II, Volume 16
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.
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. ~~~~? 5284 Phosphoryl bromide, with or without a diluent such as phosphorus tribromide or toluene,5664 has been used quite widely to make 2- or 4/6-bromopyrimidines, but there is no way to produce fluoro or iodo analogues by similar means.
In addition, ethyl yy-diethoxyacetoacetate and N-methylthiourea under the usual alkaline conditions gave in good yield only one isomer, 6-diethoxymethyl-3-methyl-2-thiouracil (1 32);6069 ethyl a-trifluoromethyl- (1 33, R = F) or a-fluoromethylacetoacetate (1 33, R = H) with S-methylthiourea gave 4-hydroxy-2- - P 3-Phenylpropionamidine 3-Methoxypropionamidine 3-Ethoxypropionamidine Benzamidine Ethyl acetoacetate Ethyl acetoacetate Ethyl acetoacetate Ethyl a-isopropylacetoacetate Ethyl 2-bromocrotonate Benzainidine Isobutyramidine Benzamidine pChlorobenzamidine Benzamidine Diethyl 2-acetylglutarate Ethyl benzoylacetate Et hy1o-toluoylacet ate Ethyl benzoylacetate Ethyl benzoylacetate Ethyl 2-acetylhept-6enoate Acetainidine Benzamidine OneCarbon Fragment Three-Carbon Fragment Aq.
Chemistry of Heterocyclic Compounds: The Pyrimidines: Supplement II, Volume 16 by Desmond J. Brown