SYNTHESIS OF NEW PYRIDO[2,3-<i>d</i>]PYRIMIDIN-5-ONES AND PYRIDO[2,3-<i>d</i>]PYRIMIDIN-7-ONES FUNCTIONALIZED AT POSITION 4 FROM 5-ACETYL-6-AMINO-4-METHYLSULFANYL-2-PHENYLPYRIMIDINE
Authors
Александр В. Комков
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia
Михаил А. Козлов
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia
Дарина И. Насырова
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia
National Research University ''Higher School of Economics'',
20 Myasnitskaya St., Moscow 101000, Russia
Андрей С. Дмитренок
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia
Игорь В. Заварзин
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky Ave., Moscow 119991, Russia
Methods were developed for the synthesis of new pyrido[2,3-d]pyrimidin-5-ones and pyrido[2,3-d]pyrimidin-7-ones from 5-acetyl-N-acyl-6-amino-4-methylsulfanyl-2-phenylpyrimidines. Heating the latter with MeONa at reflux in BuOH led to selective formation of pyrido[2,3-d]pyrimidin-5-ones or pyrido[2,3-d]pyrimidin-7-ones (containing an intact SMe group or resulting in its substitution with OBu group), depending on the nature of the acyl group. The possible substitution of SMe and OBu groups in pyridopyrimidinones was explored by using BnNH2. It was demonstrated that prior oxidation of SMe group with m-chloroperbenzoic acid allowed for simpler introduction of the NHBn moiety.
