Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part by Thomas J. Delia

By Thomas J. Delia


Pyrano- and Thiopyranopyrimidines.



Pyrimidooxazines and Pyrimidothiazines.


Chapter I Pyridopyrimidines (pages 1–117):
Chapter II Pyrano? and Thiopyranopyrimidines (pages 119–147):
Chapter III Pyrimidopyrimidines (pages 149–191):
Chapter IV bankruptcy IV: Pyrimidopyridazines (pages 193–222):
Chapter V Pyrimidooxazines and Pyrimidothiazines (pages 223–259):
Chapter VI Pyrimidotriazines (pages 261–304):

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Additional resources for Chemistry of Heterocyclic Compounds: Fused Pyrimidines Part IV: Miscellaneous Fused Pyrimidines, Volume 24

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Although this chemistry has not been thoroughly explored, the following example illustrates the utility of this method. ' 54 A number of heterocyclic rings have served as precursors to the pyrimidine portion of pyrido[2,3-d]pyrimidines. The oxadiazole ring can be viewed as a masked nitrile. 149 In one example the imbedded pyrido[2,3-d]pyrimidine nucleus, 233, was prepared initially by the reaction of 9-[(dimethylamino)chloromethylene]pyrido[ 1,Za]pyrimidine and potassium isothiocyanate. Alkylation of 233 with methyl iodide followed by treatment with ethylamine afforded the ring-cleaved 4-dimethylamino-2-ethylamino-7-methyl5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine,234.

149 H2N 150 H The condensation of 148 with fl-ketoesters, 151. s4. COZEt CH2h I 48 CHzAr 151 ______) 0 152 Pyrimidines with iodine substituted at position 5 have been found to be suitable precursors, especially in palladium catalyzed reactions. * 8 * 8 ' I COZEt R WCI2 I53 U 154" Application of this palladium coupling has also been reported with 4-chloro5-iodopyrimidines, 156, and 5-iodo-4-pyrimidones, 155,from which 156 could be obtained. 28~81 One limited example of a photochemical process has been reported.

143-146 A series of 1,2-dihydro-2-thioxo-pyrido[2,3-d]pyrimidin4(3H)-ones, 225, was synthesized by this method. 144 Methyl N-aryldithiocarbamates lead to the formation of similar products,'s3 albeit in modest yields. 157 The high-temperature condensation of 2-aminonicotinic acid, 224 (R = R' = R" = H),with N-methylformamide gives 3-methylpyrido[2,3-d]pyrimidin-4(3H)-one. s. For example, imidate esters have been allowed to react with 2-amino-3-(ethoxycarbonyl)-1,4,5,6tetrahydropyridine, 226. The products obtained are 2-substituted 5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4(3H)-ones, 227.

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