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A four-step synthesis of novel (S)-1-(heteroaryl)ethan-1-amines from (S)-Boc-alanine

Jurij Svete, Luka Šenica, Nejc Petek, Uroš Grošelj

Abstract


A series of (S)-1-(pyrimidin-4-yl)-, and regioisomeric (S)-1-(pyrazolo[1,5-a]pyrimidin-7-yl)-, and (S)-1-(pyrazolo[1,5-a]pyrimidin-5-yl)ethan-1-amines were prepared by cyclisation of (S)-N-Boc-alanine-derived ynone with N,N-1,3-dinucleophiles, such as amidines and α-aminoazoles, followed by acidolytic removal of the Boc group. Stereoselective catalytic hydrogenation of (S)-1-(pyrazolo[1,5-a]pyrimidin-7-yl)ethanamines lead to saturation of the pyrimidine ring to afford ~4:1 mixture of diastereomeric 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidines. The structures of novel compounds were elucidated with NMR.

Keywords


amines; amino acids; chirality; heterocycles; synthesis

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DOI: http://dx.doi.org/10.17344/acsi.2014.712

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