A diversity oriented, microwave assisted synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones.
A protocol for the synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones (11) is described. Thus, the formylation of a 2-aminopyridone 12 in 85% formic acid/Ac(2)O, proceeding via in situ cyclization to the intermediate formamide 13, affords the corresponding 2-hydro-4-oxo-pyridopyrimidine 14, which is converted to a 4-chloro-pyridopyrimidine 15 upon treatment with POCl(3). The subsequent transformation to the title compounds is carried by treatment with the corresponding amine in MeOH under microwave irradiation conditions.
Mont
Núria
N
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, 08017, Barcelona, Spain.
Teixidó
Jordi
J
Borrell
José I
JI
D000818:Animals; D002712:Chlorides / Q000737:chemistry; D006801:Humans; D000432:Methanol / Q000737:chemistry; D008872:Microwaves; D008956:Models, Chemical; D015394:Molecular Structure; D017553:Phosphorus Compounds / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D020794:Receptor Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship; D044366:Transition Temperature
D002712:Chlorides; D017553:Phosphorus Compounds; D011728:Pyridones; D011743:Pyrimidines; D020794:Receptor Protein-Tyrosine Kinases; C043693:phosphorus chloride; D000432:Methanol