Production of pyrrolopyrimidines

Details Production of pyrrolopyrimidines Production of pyrrolopyrimidines

1993-03-08

1994-09-20

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C07D48704

Patent

active

053490649

ABSTRACT:
There is provided an improved process for producing novel compounds represented by the general formula: ##STR1## wherein the ring A represents a pyrrole ring which may be hydrogenated; X represents an amino, hydroxyl or mercapto group; R.sup.1, R.sup.2 and R.sup.3 each being the same as or different from the other, represents hydrogen or an alkyl, alkenyl or alkynyl group which may be substituted; R.sup.4 represents OR.sup.5 wherein R.sup.5 represents hydrogen or a hydrocarbon group which may be substituted or NHCH(COOR.sup.6)CH.sub.2 CH.sub.2 COOR.sup.7 wherein R.sup.6 and R.sup.7 each represents hydrogen or a hydrocarbon group which may be substituted; and n represents an integer of 1 to 4, or a salt thereof from compounds represented by the general formula: ##STR2## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are the same as defined above; Y.sup.1 and Y.sup.2 each represents oxygen or sulfur atom; R.sup.8 and R.sup.9 each, being the same as or different from the other, represents a hydrocarbon group which may be substituted, or salts thereof by an intramolecular ring closure reaction to form a pyrrolopyrimidine ring and, if necessary, reducing the pyrrole ring thus formed to a pyrroline ring. The compounds are useful as antitumor agents.

REFERENCES:
Journal of the Chemical Society, 1960, Part I, pp. 131-138, J. Davoll, Pyrrolo[2,3-d]pyrimidines.
Agricultural and Biological Chemistry, vol. 41, 1977, pp. 1501-1507, T. Kondo et al. "Synthesis of 5-Methyltubercidin and Its .alpha.-Anomer via Condensation of the Anion of 4-Methoxy-5-methyl-2-methyl-thiopyrrolo [2,3-d]pyrimidine and 2,3,5-Tri-O-benzyl-D-ribofuranosyl Bromide".
Chemical Abstracts, vol. 112, No. 11, Mar. 12, 1990, p. 815, 99168b.
Chemische Berlichte, vol. 110 (1977) pp. 1462-1469 (translation), 1977.
"The Chemistry of the Carbonyl Group", vol. 2, (1970) Interscience Publishers, pp. 19-20, 1970.
"Advanced Organic Chemistry" by March pp. 796-797 (1985) published by John Wiley and Sons.
"Rodd's Chemistry of Carbon Compounds" edited by Coffey vol. IV, Part A, pp. 329-333, 402-403 (1973) Elsevier Scientifc Publishing Company.

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