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Generated: December 13, 2017

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Title: Process for the synthesis of 2'-O-substituted pyrimidines
Abstract:Improved processes for the synthesis of 2'-O-substituted pyrimidine nucleosides are provided. The processes feature alkylation of a 2,2'-anhydropyrimidine nucleoside or a 2S,2'-anhydropyrimidine nucleoside with a weak nucleophile in the presence of a Lewis acid.
Inventor(s): Cook; Phillip Dan (San Marcos, CA), Springer; Robert H. (Carlsbad, CA), Sprankle; Kelly G. (Vista, CA), Ross; Bruce S. (Carlsbad, CA)
Assignee: Isis Pharmaceuticals, Inc. (Carlsbad, CA)
Filing Date:Jul 09, 1997
Application Number:08/890,084
Claims:1. A process for the synthesis of a 2'-O-substituted pyrimidine nucleoside of formula: ##STR5## wherein: Q is a pyrimidine base or a 2-S pyrimidine base;

R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.30 alkenyl, C.sub.1 -C.sub.30 alkynyl, C.sub.6 -C.sub.14 aryl, or C.sub.7 -C.sub.30 aralkyl, wherein said substitution is halo, amino, hydroxyl, thiol, ether or thioether; and

R.sup.2 and R.sup.3 are independently hydrogen or a hydroxyl protecting group;

comprising the steps of:

providing a 2-2'-anhydropyrimidine nucleoside;

selecting an alcohol of the formula R.sup.1 -OH; and

treating said 2-2'-anhydropyrimidine nucleoside and said alcohol with a Lewis acid under conditions of time, temperature and pressure effective to yield said 2'-O-substituted pyrimidine nucleoside.

2. The process of claim 1 wherein said 2-2'-anhydropyrimidine nucleoside and said alcohol are treated in a pressure sealed vessel.

3. The process of claim 1 wherein R.sup.1 is C.sub.1 -C.sub.10 alkyl.

4. The process of claim 1 wherein R.sup.1 is C.sub.6 -C.sub.14 aryl.

5. The process of claim 1 wherein said treating comprises heating at from about 120.degree. C. to about 200.degree. C.

6. The process of claim 1 wherein said pyrimidine nucleoside is uridine or 5-methyluridine.

7. A process for the synthesis of a 2'-O-substituted cytidine nucleoside of formula: ##STR6## wherein: X is O or S;

R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.30 alkenyl, C.sub.1 -C.sub.30 alkynyl, C.sub.6 -C.sub.14 aryl, or C.sub.7 -C.sub.30 aralkyl, wherein said substitution is halo, amino, hydroxyl, thiol, ether or thioether;

R.sup.2 and R.sup.3 are independently hydrogen or a hydroxyl protecting group;

R.sup.5 and R.sup.6 are independently H, C.sub.1 -C.sub.30 hydrocarbyl or substituted C.sub.1 -C.sub.30 hydrocarbyl;

comprising the steps of:

providing a 2-2'-anhydrouridine nucleoside of formula: ##STR7## selecting an alcohol of formula R.sup.1 -OH; treating said 2-2'-anhydrouridine nucleoside and said alcohol with a Lewis acid under conditions of time, temperature and pressure effective to form a 2'-O-substituted uridine nucleoside; and

aminating said 2'-O-substituted uridine nucleoside to said 2'-O-substituted cytidine nucleoside.

8. The process of claim 12 wherein said 2-2'-anhydrouridine nucleoside and said alcohol are treated in a pressure sealed vessel.

9. The process of claim 7 wherein R.sup.1 is C.sub.1 -C.sub.10 alkyl.

10. The process of claim 7 wherein R.sup.1 is C.sub.6 -C.sub.14 aryl.

11. The process of claim 7 wherein said treating comprises heating from about 120.degree. C. to about 200.degree. C.

12. The process of claim 7 wherein said 2'-O-substituted cytidine nucleoside is 2'-O-methyl-5-methylcytidine.
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