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

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.

Read article: Acta Chimica Slovenica, 2015, 62, 60-71