67362-37-2Relevant academic research and scientific papers
Two-step synthetic approach to 6-substituted pyrido[2,3-d]pyrimidine(1H,3H) -2,4-diones from 6-amino-, 6-alkylamino-, and 6-arylamino-1,3-dimethyluracils
Bischoff, Kerstin,Girreser, Ulrich,Heber, Dieter,Schütt, Martin
, p. 486 - 494 (2007/10/03)
The Mannich reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines 3, easily accessible by condensation of 6-amino-1,3-dimethyluracil (1) with Mannich bases 2a-c, gives rise to a mixture of 7-aryl-6-(N,N-dimethylaminomethyl) pyrido[2,3-d]pyrimidines 6 and
Synthesis of 6-substituted 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidine(1H,3H) -2,4-diones using the Vilsmeier reaction
Girreser, Ulrich,Heber, Dieter,Schütt, Martin
, p. 11511 - 11517 (2007/10/03)
The reaction of 6-amino-1,3-dimethyluracil with equimolar amounts of arylalkanone Mannich bases under optimized reaction conditions leads to 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines in a yield of 50-80%. Functionalization of these dihydropyridopyrimidine(1H,3H)-2,4-diones with the Vilsmeier reagent affords, depending on the reaction conditions, either 6-dimethylaminomethylidene substituted 5H-pyrido[2,3-d]pyrimidine(1H,3H)-2,4- diones or the corresponding pyridopyrimidine(1H,3H)-2,4-diones bearing a carboxaldehyde function in position 6 of the heterocycle. Some further transformations of the aldehyde function demonstrate the synthetic potential of the synthesized structures, introducing pharmacologically relevant basic substituents into the side chain of these pyrido[2,3-d]pyrimidine derivatives. The reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones with phosphorous oxychloride and N,N-dimethylformamide affords either the shown 6-dimethylaminomethylidene substituted heterocycle or the corresponding pyridopyrimidine(1H,3H)-2,4-dione bearing a carboxaldehyde function. These compounds are suitable structures for further modifications by introducing pharmacologically relevant substituents.
