Method for preparation of optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acids
AssigneeE. I. Du Pont de Nemours and Company
InventorRAFAEL SHAPIRO
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Abstract
A new method for the preparation of optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid compounds of Formula 1 is disclosed wherein R1 is H or an optionally substituted carbon moiety. Also disclosed is the method comprising additional steps to prepare optionally substituted 4-pyrimidinecarboxylic acids and esters using the compound of Formula 1 as an intermediate.
Claims19
1-25. (canceled)
A method for preparing a compound of Formula 1 or 1a
- wherein R1 is optionally substituted cyclopropyl or an optionally substituted phenyl;
- comprising the steps of:
- (1) contacting a mixture comprising (a) a compound of Formula 2a
- wherein M is alkali metal and R2 and R3 are independently C1-C4 alkyl, (b) a C1-C4 alkanol, and (c) a first portion of water, with a solution comprising a first base and a second portion of water, said base being in an amount sufficient to create a first resultant solution having a pH ranging from about 10 to about 14, said first resultant solution comprising a compound of Formula 2b,
- wherein M and R3 are defined as above for Formula 2a;
- (2) contacting the first resultant solution comprising the compound of Formula 2b with a compound of Formula 3 or an acid salt thereof or with a solution comprising a compound of Formula 3 or an acid salt thereof,
- wherein R1 is defined as above for Formula 1, and a second base in an amount sufficient to create a second resultant solution having a pH ranging from about 9 to about 12, said second resultant solution comprising a salt of the compound of Formula 1;
- and
- (3) adding an acid to the second resultant solution comprising the salt of the compound of Formula 1 to form the compound of Formula 1.
A method for preparing a compound of Formula 4 or 4a
- wherein R1 is optionally substituted cyclopropyl or an optionally substituted phenyl, comprising the method of claim 1 and a further step comprising contacting the compound of Formula 1 with a chlorinating agent.
A method for preparing a compound of Formula 6
- wherein R1 is optionally substituted cyclopropyl or an optionally substituted phenyl, comprising the method of claim 14 and a further step comprising contacting the compound of Formula 4 or 4a with a chloride displacement agent
A method for preparing a compound of Formula 7
- wherein R1 is optionally substituted cyclopropyl or an optionally substituted phenyl, comprising the method of claim 15 and a further step comprising contacting the compound of Formula 6 with ammonia.
A method of preparing a compound of Formula 8
- wherein R1 is optionally substituted cyclopropyl or an optionally substituted phenyl;
- and R4 is C1-C14 alkyl, C2-C14 alkoxyalkyl, C2-C14 hydroxyalkyl or benzyl;
- comprising the method of claim 16 and an additional step of contacting the compound of Formula 7 with an R4 transfer agent.
The method of claim 7 wherein R4 is C1-C8 alkyl or C2-C8 alkoxyalkyl.
A compound of Formula 5a
Dependencies are inferred from the claim text.