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Details for Patent: 5,760,202

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Details for Patent: 5,760,202

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:Jun 07, 1995
Application Number:08/475,467
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; wherein said Lewis acid is a borate.

2. The process of claim 1 wherein said borate is a trialkyl borate.

3. The process of claim 2 wherein the formula of said trialkyl borate is B(OR.sup.1).sub.3.

4. The process of claim 3 wherein said trialkyl borate is prepared from the treatment of borane with an alcohol.

5. 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 form said 2'-O-substituted cytidine nucleoside;

wherein said Lewis acid is a borate.

6. The process of claim 5 wherein said borate is a trialkyl borate.

7. The process of claim 6 wherein the formula of said trialkyl borate is B(OR.sup.1).sub.3.

8. The process of claim 6 wherein said trialkyl borate is prepared from the treatment of borane with an alcohol.
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