Abstract
Pyrimidines are compounds with a wide range of biological activities, and the synthesis of pyrimidine derivatives—useful in chemical and medicinal applications—is important in medicinal chemistry. This work shows the synthesis under microwave irradiation of the novel compound ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate (3) from (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) and acetylacetone (2). Compound 3 was easily purified, obtained in moderate yield (70%), and fully characterized by UV-Vis, FTIR-ATR spectroscopy, 1H-NMR, 13C-NMR, HRMS, and EI-MS.
Highlights
Pyrimidines are diazine compounds produced by substituting two nitrogen atoms at positions 1 and 3 of a six-membered ring (1,3-diazine) [1]
We used the (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) as a source of amine group to be condensed with acetylacetone (2) under microwave irradiation to synthesize the new ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate
This study shows the synthesis of ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]
Summary
Pyrimidines are diazine compounds produced by substituting two nitrogen atoms at positions 1 and 3 of a six-membered ring (1,3-diazine) [1]. Due to the biological activities of pyrimidines, their synthesis is currently engaged in medicinal chemistry. The principal method of pyrimidine synthesis involves the condensation of β-dicarbonyl and amine compounds [14]. In this sense, α-amino acids show high enantiomeric purity and are versatile building blocks for synthesizing heterocyclic systems [15,16]. The guanidine group is rarely used in such reactions, despite its wide use as an N,N-binucleophile to synthesize heterocyclic nitrogen systems [22,23]. We used the (S)-N-α-benzoyl-l-arginine ethyl ester hydrochloride (1) as a source of amine group to be condensed with acetylacetone (2) under microwave irradiation to synthesize the new ethyl (S)-2-benzamido-5-[(4,6-dimethylpyrimidin-2-yl)amino]pentanoate
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