Process for the preparation of fused pyridine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

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546298, 546341, 560 37, 560 47, 560104, 560117, C07D47104

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048188190

ABSTRACT:
2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a haloaromatic compound and an unsaturated compound in the presence of a palladium catalyst. The products are chemical intermediates for the preparation of antineoplastic agents.
A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.

REFERENCES:
patent: 3856959 (1974-12-01), Mead
patent: 4172200 (1979-10-01), Piper et al.
patent: 4369319 (1983-01-01), DeGraw et al.
patent: 4431805 (1985-02-01), Temple et al.
patent: 4432981 (1984-02-01), Lesher et al.
patent: 4460591 (1984-07-01), DeGraw et al.
patent: 4512992 (1985-04-01), Duch et al.
patent: 4526964 (1985-07-01), Temple et al.
patent: 4532241 (1985-07-01), DeGraw et al.
patent: 4536575 (1985-08-01), Temple et al.
patent: 4564616 (1986-01-01), Jones et al.
R. F. Heck, J. Amer. Chem. Soc., 90, pp. 5518-5526 (1968).
Advanced Organic Chemistry by Jerry March (2nd Ed). McGraw-Hill, Publishers (New York) p. 656 (1977).
Frank et al., J. Org. Chem. 43, p. 2947 (1978).
Sonagashira et al., Tetrahedron Lett. 50, p. 4467 (1975).
Moad et al., JACS 101:20, 6068-6076 (9/27/76).
Jahine et al., Ind. J. Chem., 16B, 889-891 (10/78).
Sirotnak et al., Cancer Treat. Rep., 66:2 (2/82).
Troschutz et al., Arch. Pharm. 311, 406-414 (1978).
Temple et al., J. Org. Chem 47, 761-764.
Taylor et al., J. Org. Chem. 50, 1010-1014 (1985).
Taylor et al., Chem. & Biology of Pteridines (Ed. J. A. Blair) 1983 Walter de Gruyter & Co., N.Y. 115-119.
Taylor et al., J. Org. Chem. 48, 4852-4860 (1983).
Taylor et al., J. Org. Chem. 50, 1005-1010 (1985).
DeGraw et al., J. Heterocycl. Chem. 19, 1461-1463 (1982).
Grivsky et al., J. Med. Chem. 23:3, 327-329 (1980).
Piper et al., J. Med. Chem. 23, 320-321 (1980).
DeGraw et al., J. Med. Chem 17:5, 552-553 (1974).
Elliott et al., J. Med. Chem. 17:5, 553-555 (1974).
Nair. J. Org. Chem., 50, 1879-1884 (1985).
Drugs of the Future, IV, No. 9, 641-644 (1979).
Sirotnak et al., Cancer Treat. Rep. 62:7, 1047-1052 (1978).
Stone et al., Biochem. Pharmac, 33:2, 175-179 (1984).
Srinivasan et al., J. Org. Chem., 45, 3746-3748 (1980).
Hurlbert et al., J. Med. Chem., 11, 703-707 (1968).
Hurlbert et al., J. Med. Chem., 11, 708-710 (1968).
Hurlbert et al., J. Med. Chem., 11, 711-717 (1968).
Rosowsky et al., J. Med. Chem., 17:12, 1272-1276 (1974).
Struck et al., J. Med. Chem., 14:8, 693-695 (1971).
CA 96:104757a (1982) Sirotnak et al.
Taylor et al., J. Med. Chem. 28:7, 914-921 (1985).
DeGraw et al., J. Heterocycl. Chem. 8, 105-110 (1971).
Oakes et al., J. Chem. Soc. (London) 4433 (1956).
Elsager et al., Lectures in Heterocyclic Chemistry, vol. 2, S-97; Supplement to J. Heterocyclic Chem., 11 (1974).
Harrington, Synthetic Approaches to 5-Deaza and 5,10-Dideazafolic Acid Analogs, Ph. D. Dissertation, Princeton U., 1982.
DeGraw et al., J. Med. Chem., 17:470 (1974).
DeGraw et al., J. Heterocyclic Chem., 13:439 (1976).
Smith et al., Biochem. 20: 1241 (1981).
Temple et al., J. Med. Chem. 24:1254 (1981).
DeGraw et al., Chem. & Biolog. of Pteridines (Ed. Kisliuk/Brown) 1979 Elsevier, North Holland (229-234).
Srinivasan et al., J. Org. Chem. 46: 1777 (1981).
Srinivasan et al., Tetrahedron Lett. 23:1431 (1982).
Wheeler et al., J. Amer. Chem. Soc. 74:4725 (1952).
Kisliuk, R. L., Nature, 188:584 (1960).
Kisliuk et al., J. Biol. Chem. 239: 1900 (1964).
Horwitz et al., J. Med. Chem. 11:907 (1968).
Melpoler et al., J. Org. Chem. 41, No. 2, 1976, 265.
Chalk et al., J. Org. Chem. 41, No. 7, 1976, 1206.
Arai et al., J. Heterocyclic Chem., 15, 351 (1976).
Tamaru et al., Tetrahedron Papers 10, 919 (1978).
Tamaru et al., Tetrahedron, 35, 329 (1979).

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