e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Ring transformation of pyrimidines to pyridines. Synthesis of 4??alkylaminopyridin??2??ones by alkaline hydrolysis of 6??(2??dimethylaminovinyl) uracils

…, T Asao, S Senda, Y Kitade, Y Maki

Index: Hirota, Kosaku; Abe, Yoshio; Asao, Tetsuji; Senda, Shigeo; Kitade, Yukio; Maki, Yoshifumi Journal of Heterocyclic Chemistry, 1988 , vol. 25, p. 985 - 990

Full Text: HTML

Citation Number: 9

Abstract

Abstract Alkaline hydrolysis of 1, 3-disubstituted 6-(2-dimethylaminovinyl) uracils 2 induced a novel ring transformation giving 4-alkylaminopyridin-2-ones 3 via ring-opening and ring- closure processes. The 4-methylamino-3-nitropyridin-2-one (3a) thus obtained was employed for the synthesis of 3-deazahypoxanthine derivative 8. 4-Alkylamino-3- cyanopyridin-2-ones 11, ricinine analogs, were also prepared by the reaction of 4-chloro- ...

(E)-6-(2-(dimethylamino)vinyl)-3-methyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

(E)-6-(2-(dimet...

~81%

4-anilino-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-anilino-1-met...

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

Structure

~79%

4-anilino-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-anilino-1-met...

RICININIC ACID Structure

~%

4-anilino-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-anilino-1-met...

5-cyano-3,6-dimethyl-1-phenyluracil Structure

5-cyano-3,6-dim...

~%

4-anilino-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-anilino-1-met...

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

Dimethylamine Structure

~75%

4-(dimethylamino)-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-(dimethylamin...

RICININIC ACID Structure

~%

4-(dimethylamino)-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-(dimethylamin...

RICININIC ACID Structure

~86%

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

(E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2,4-dione Structure

(E)-6-(2-(dimet...

~96%

5-Nitro-6-methyluracil Structure

5-Nitro-6-methy...

(E)-6-(2-(dimethylamino)vinyl)-3-ethyl-1-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

(E)-6-(2-(dimet...

~52%

N/A Structure

1-ethyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-ethyl-4-(meth...

3-ethyl-1,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

3-ethyl-1,6-dim...

~%

1-ethyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-ethyl-4-(meth...

1,3-dimethyl-6-(2-dimethylaminovinyl)-5-nitrouracil Structure

1,3-dimethyl-6-...

~13%

1-methyl-4-(methylamino)-3-nitropyridin-2-one Structure

1-methyl-4-(met...

(4E)-1,3-dimethyl-4-(nitromethylidene)pyrimidin-2-one Structure

(4E)-1,3-dimeth...

1,3-dimethyl-6-(2-dimethylaminovinyl)-5-nitrouracil Structure

1,3-dimethyl-6-...

~60%

1-methyl-4-(methylamino)-3-nitropyridin-2-one Structure

1-methyl-4-(met...

(4E)-1,3-dimethyl-4-(nitromethylidene)pyrimidin-2-one Structure

(4E)-1,3-dimeth...

(E)-6-(2-(dimethylamino)vinyl)-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione Structure

(E)-6-(2-(dimet...

~54%

4-anilino-1-methylpyridin-2-one Structure

4-anilino-1-met...

6-(2-dimethylaminovinyl)-1,3-dimethyluracil Structure

6-(2-dimethylam...

~86%

1,3,6-trimethyluracil Structure

1,3,6-trimethyl...

6-[(E)-2-(dimethylamino)vinyl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

6-[(E)-2-(dimet...

~79%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

N/A Structure

6-[(E)-2-(dimethylamino)vinyl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

6-[(E)-2-(dimet...

~47%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

2-cyano-5-dimethylamino-N-methyl-3-methylamino-2,4-pentadienamide Structure

2-cyano-5-dimet...

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

methylamine Structure

~79%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

5-cyano-1,3,6-trimethyl-2,4(1H,3H)-pyrimidinedione Structure

5-cyano-1,3,6-t...

~%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

2-cyano-5-dimethylamino-N-methyl-3-methylamino-2,4-pentadienamide Structure

2-cyano-5-dimet...

~%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

RICININIC ACID Structure

~%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

6-[(E)-2-(dimethylamino)vinyl]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Structure

6-[(E)-2-(dimet...

~%

1-methyl-4-(methylamino)-2-oxopyridine-3-carbonitrile Structure

1-methyl-4-(met...

Propylamine Structure

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

~59%

1-methyl-2-oxo-4-(propylamino)pyridine-3-carbonitrile Structure

1-methyl-2-oxo-...

RICININIC ACID Structure

~%

1-methyl-2-oxo-4-(propylamino)pyridine-3-carbonitrile Structure

1-methyl-2-oxo-...

4-chloro-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-chloro-1-meth...

n-butylamine Structure

~74%

4-(butylamino)-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-(butylamino)-...

RICININIC ACID Structure

~%

4-(butylamino)-1-methyl-2-oxopyridine-3-carbonitrile Structure

4-(butylamino)-...