Process to prepare pyrimidine nucleosides

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

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544247, C07D49816

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active

050774034

ABSTRACT:
A process for the production of a compound of the formula ##STR1## where R.sub.1 and R.sub.2 each are alkyl C.sub.1 -C.sub.16, aryl, aralkyl, alkenyl, alkynyl, cyano, carboxy and esters, carboximido, N-monosubstituted and N,N-disubstituted carboximido with alkyl, aralkyl, and aryl groups; R.sub.3 is tertiary butyldimethyl silyl, R.sub.4 is tertiarybutyldimethylsilyl, trimethylsilyl, X=O or NH comprising condensing a compound of the formula ##STR2## wherein R.sub.3 and R.sub.4 are as defined above with a compound of either the formula: ##STR3## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.5 is C.sub.1 -C.sub.4 ; in the presence of a reaction-inert solvent at a temperature of from 50.degree.to about 150.degree. C. forming an intermediate and oxidizing the intermediate product, to form the desired compound of formula I. The products are antiviral.

REFERENCES:
Hall, Charles M., et al., "The Synthesis of O.sup.2,2 -Anhydro-5, 6-dihydro Nucleosides", J. Org. Chem. vol. 37, No. 21, 1972, pp. 3290-3293.
Hall et al., J. Org. Chem., vol. 37, No. 21, 1972 pp. 3290-3293.
Ryuzi et al., Chemical Abstract vol. 69, 1968; 524502.

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