THIOPTERIDINES AND PROCESS FOR PRODUCING SAME

• US 3,859,287 A
• Filed: 05/05/1971
• Issued: 01/07/1975
• Est. Priority Date: 05/05/1971
• Status: Expired due to Term

• Current Assignee: Broadbent H. Smith, Walter Wesley Parish
• Original Assignee: Broadbent H. Smith, Walter Wesley Parish
• Inventors: Parish, Walter Wesley, Broadbent, H. Smith
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): Tighe, Anne Marie T.
• Application Number:
  US05/140,536
• Time in Patent Office: 1,343 Days
• Field of Search: 260/251.5
• US Class Current: 544/260
• CPC Class Codes: C07D 475/06 with a nitrogen atom directly attached in position 4
• CPC Class Codes: C07D 475/08 with a nitrogen atom directly attached in position 2
• CPC Class Codes: C07D 475/10 with an aromatic or hetero-aromatic ring directly attached in position 2
• CPC Class Codes: C09K 11/06 containing organic luminescent materials

Abstract

Novel 6-thio-substituted pteridine and related compounds of the pteridine family described by the following formula have been produced directly from reaction of substituted 5nitrosopyrimidines and pyridinium salts in the presence of a thiol. The novel 6-thio substituted compounds of the pteridine family may be represented by the general formula

D R A W I N G
WHERE R2, R4 and R6 are amino, alkyl amino, arylamino, acetamido, hydroxy alkoxy, aryloxy, thio, alkylthio, arylthio, alkyl, aryl or hydrogen. When R2, R4 or R6 are chalcogens, i.e., hydroxy or thio (x O or S) then R1, R3 and R7 may be hydrogen, alkyl or aryl. R5 may be an organic or inorganic group although preferably an organic group, especially alkyl and aryl groups included substituted alkyl and aryl groups. Inorganic groups include metals such as alkali and alkaline earth metals. The alkyl and aryl groups are perferably lower alkyl and single-ring aryl groups, especially alkyl groups of less than 6 carbon atoms and substituted phenyl groups wherein the substituent on the phenyl group is a lower alkyl group or a halogen radical.

Claims

1. A THIOPTERIDINE OF THE STRUCTURE

2. A process for producing 2,4,-substituted-6 thiopteridines comprising the steps of reacting:

a. a thiol selected from the class consisting of alkyl and aryl thiols having less than ten carbon atoms, b. a 2-substituted -4,6-diacetamido-5-nitropyrimidine, wherein the substitutent in the 2 position is selected from the group consisting of amino, lower alkyl amino phenylamino, acetAmido, hydroxy, lower alkoxy, phenoxy, thio, lower alkyl thio, phenylthio, lower alkyl, phenyl or hydrogen and c. a quaternary pyridinium halide selected from the class consisting of

3. The thiopteridine of claim 2 wherein R is phenyl.

4. The thiopteridine of claim 2 wherein R is methyl.

5. The thiopteridine of claim 2 wherein R is t-butyl.

6. A process for producing 2,4,-substituted-comprising the steps of reacting in the presence of a solvent for said reactants and an alkali metal base a. a thiol selected from the class consisting of alkyl and aryl thiols having less than ten carbon atoms, b. a 2,4,6-substituted-5-nitrosopyrimidine wherein the substituent in the 4 position is selected from the class consisting of amino and acetamido and wherein the substituents in the 2 and 6 positions are selected from the group consisting of amino, lower alkyl amino, phenylamino, acetamido, hydroxy, lower alkoxy, phenoxy, thio, lower alkyl thio, phenylthio, lower alkyl, phenyl or hydrogen, and c. a quaternary pyridinium compound selected from the class consisting of pyridinium-activated aldehydes, ketones, nitriles, acids, amides and esters, said compound having a reactive methylene group adjacent to the functional group.

7. The process of claim 6 wherein the thiol is an alkyl or aryl thiol having less than 10 carbon atoms.

8. The process of claim 6 wherein the 2,4,6-substituted-5-nitrosopyrimidine compound is a 2-substituted-4,6-diacetamido-5-nitrosopyrimidine wherein the substituent in the 2 position is selected from the group consisting of amino, lower alkyl amino, phenylamino, acetamido, hydroxy, lower alkoxy, phenoxy, thio, lower alkyl thio, phenylthio, lower alkyl, phenyl or hydrogen.

9. The process of claim 8 wherein the 5-nitrosopyrimidine is 2-amino-4,6-diacetamido-5-nitrosopyrimidine.

10. The process of claim 9 wherein the 5-nitrosopyrimidine is 2, 4,6-triamino-5-nitrosopyrimidine.

11. The process of claim 6 wherein the quaternary compound is 1-(cyanomethyl) pyridinium halide.

12. The process of claim 6 wherein the quaternary pyridinium compound is 1-(carboxy alkyl) pyridinium halide wherein the alkyl group has less than about 10 carbon atoms.

13. The 6-thiosubstituted pteridine of claim 1 wherein R'"'"''"'"''"'"''"'"' is acetamido.

14. The 6-thiosubstituted pteridine of claim 1 wherein R'"'"''"'"''"'"''"'"' is amino.

15. The 6-thiosubstituted pteridine of claim 1 wherein R is phenyl.

16. The 6-thiosubstituted pteridine of claim 1 wherein R'"'"''"'"''"'"''"'"''"'"''"'"' is amino.