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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

General and Facial Synthesis of 2‐Amino‐5‐halogenpyrimidine‐4‐carboxylic Acids and Their Derivatives

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Pages 2231-2241 | Received 04 Nov 2006, Published online: 03 Jul 2007

References

  • Kleemann , A. , Engel , J. , Kutscher , B. and Reichert , D. 2001 . Pharmaceutical Substances 2004 Stuttgart : Thieme . 2115
  • Danjou , E. P. , Molinier , P. , Berlin , I. , Patat , A. , Rosenzweig , P. and Morselli , P. L. 1992 . Assessment of the anticholinergic effect of the new antihistamine mizolastine in healthy subjects . Brit. J. Clin. Pharmacol. , 34 ( 4 ) : 328 – 331 .
  • Rosenzweig , P. , Thebault , J. J. , Caplain , H. , Dubruc , C. , Bianchetti , G. , Fuseau , E. and Morselli , P. L. 1992 . Annals Allergy , 69 ( 2 ) : 135 – 139 .
  • Kukla , M. J. , Ludovici , D. W. , Kavash , R. W. , De Corte , B. L. D. , Heeres , J. , Janssen , P. A. J. , Koymans , L. M. H. , De Jonge , M. R. , Van Aken Koen , J. A. , Krief , A. and Leenders , R. G. G. Preparation of substituted amino pyrimidines and triazines as HIV replication inhibitors . WO, 0185700 . 2001 . Chem. Abstr., 2001, 135, 371765
  • Lubisch , W. , Moeller , A. , Treiber , H.‐J. and Knopp , M. New substituted heterocyclic amides, their preparation and application . DE, 19817459 . 1999 . Chem. Abstr., 1999, 131, 299438
  • Narr , B. , Roch , J. , Mueller , E. and Haarmann , W. Pyrimidine derivatives . DE, 2341925 . 1975 . Chem. Abstr., 1975, 83, 43369
  • Jimenez , B. M. , Kranz , P. , Lee , C. S. , Gero , A. M. and O'Sullivan , W. J. 1989 . Inhibition of uridine phosphorylase from Giardia lamblia by pyrimidine analogs . Biochem. Pharmacol. , 38 : 3785 Chem. Abstr. 1990, 112, 195107
  • Gero , A. M. , O'Sullivan , W. J. and Brown , D. 1985 . Human spleen dihydroorotate dehydrogenase: A study of inhibition of the enzyme . Biochem. Med. , 34 : 60 Chem. Abstr. 1985, 103, 156291
  • Dunbar , P. G. , Durant , G. J. , Rho , T. , Ojo , B. , Huzl , J. J. III , Smith , D. A. , El‐Assadi , A. A. , Sbeih , S. , Ngur , D. O. , Periyasamy , S. , Hoss , W. and Messer , W. S. Jr. 1994 . Design, synthesis, and neurochemical evaluation of 2‐amino‐5‐(alkoxycarbonyl)‐3,4,5,6‐tetrahydropyridines and 2‐amino‐5‐(alkoxycarbonyl)‐1,4,5,6‐tetrahydropyrimidines as M1 muscarinic receptor agonists . J. Med. Chem. , 37 : 2774
  • Muzi , S. and Abdul‐Rahman , S. Novel compounds, specifically aromatic and heteroaromatic ureas and thioureas, useful against parasites and especially against coccidiosis . WO, 0130749 . 2001 . Chem. Abstr., 2001, 134, 340357
  • Jart , A. 1963 . Infrared spectra of carboxylic acid derivatives. I. S‐Benzylthiouronium salts. II. p‐Bromophenacyl esters . Acta Polytech. Scand. Chem. Metall. Ser. , 24 : 120
  • Bray , H. G. , Thorpe , W. V. and Wood , P. B. 1951 . Fate of certain organic acids and amides in the rabbit, XII: Aminohydroxybenzoic acids . Biochem. J. , 48 : 394 – 399 .
  • Volovenko , Y. M. and Blyumin , E. V. 1998 . Nucleophilic substitution in a series of 2‐methylsulfonyl‐5‐chloropyrimidine‐4‐carboxylic acid derivatives . Chem. Heterocycl. Compd. (NY) , 34 : 324 – 328 .
  • Volovenko , Y. M. and Blyumin , E. V. 2000 . Nucleophilic substitution in some 5‐chloropyrimidines: Synthesis and properties of condensed pyridopyrimidines . Tetrahedron , 56 : 5185
  • Volovenko , Y. M. , Blyumin , E. V. , Volovnenko , T. A. , Shokol , T. V. and Shishkin , O. V. 2004 . 2‐(3,4‐Dihydro‐4‐oxo‐2‐quinazolinyl)acetonitriles in the synthesis of new condensed pyrimidines . Synthesis , 16 : 2659 – 2664 .
  • Brown , D. J. 1994 . “ The Pyrimidines ” . In Chemistry Heterocylic Compounds New York : Wiley .
  • Bessard , Y. and Stucky , G. Process for the preparation of substituted pyrimidines . EP, 802,193 . 1997 . Chem. Abstr., 1997, 127, 358872
  • Miyashita , A. , Suzuki , Y. , Otha , K. and Higashino , T. 1994 . Preparation of heteroarenecarbonitriles by reaction of haloheteroarenes with potassium cyanide with sodium p‐toluenesulfinate as catalyst . Heterocycles , 39 : 345 – 356 .
  • Bessard , Y. and Crettaz , R. 2000 . Rate acceleration of nucleophylic substitution of 2‐chloro‐4,6‐dimethoxypyrimidine by sulfinate catalysis . Tetrahedron , 56 : 4739 – 4745 .
  • Grant , G. A. , Seemann , C. V. and Winthrop , S. O. 1956 . Basic esters of substituted pyrimidine‐4‐carboxylic acids . Can. J. Chem. , 34 : 1444 – 1446 .
  • McOmie , J. F. W. and White , I. M. 1953 . Pyrimidines: VI: 5‐Bromopyrimidine . J. Chem. Soc. , : 3129 – 3131 .
  • Liang , Y. M. , Luo , S. J. , Zhang , Z. X. and Ma , Y. X. 2002 . Efficient synthesis of a new pyrimidine derivative . Synth. Commun. , 1 : 153 – 158 .
  • Budesinsky , Z. , Vavrina , J. , Langsadl , L. and Holubek , J. 1980 . On the synthesis of 4‐ and 5‐pyrimidinyldiphenyl‐(1‐imidazolyl)methanes and their antifungal activity . Collect. Czech. Chem. Commun. , 45 : 539 – 547 .
  • Blyumin , E. V. and Volovenko , Y. M. 2000 . Reactions of 5‐chloro‐2‐methylsulfonyl‐4‐pyrimidinecarboxylic acid and its esters with amines: The inversion of reactivity in a pyrimidine ring . Mendeleev. Commun. , 6 : 237 – 238 . The possibility of the synthesis of type 5 compounds (by the example of 5b, 5f, 5h) from 6a has been outlined in
  • Fliri , A. F. J. , Sanner , M. A. , Seymour , P. A. and Zorn , S. H. Dopamine D4 ligands for the treatment of novelty‐seeking disorders . EP, 1177792 . 2002 . Chem. Abstr., 2002, 136, 145264
  • Tabuchi , T. , Yamamoto , T. and Nakayama , M. Preparation of aryl‐ or heterocyclylsulfonamide derivatives as agricultural and horticultural microbicides . WO, 0065913 . 2000 . Chem. Abstr., 2000, 133, 350233
  • Beight , D. W. , Craft , T. J. , Denny , C. P. , Franciskovich , J. B. , Goodson , T. Jr. , Hall , S. E. , Herron , D. K. , Joseph , S. P. , Klimkowski , V. J. , Masters , J. J. , Mendel , D. , Milot , G. , Pineiro‐Nunez , M. M. , Sawyer , J. S. , Shuman , R. T. , Smith , G. F. , Tebbe , A. L. , Tinsley , J. M. , Weir , L. C. , Wikel , J. H. , Wiley , M. R. and Yee , Y. K. Preparation of heteroaryl‐substituted aromatic amides as factor Xa inhibitors . WO, 0039118 . 2000 . Chem. Abstr., 2000, 133, 89437

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