132575-27-0Relevant articles and documents
C-Nucleoside Studies. Part 21. Synthesis of Some Hydroxyalkylated Pyrrolo- and Thieno-pyrimidines Related to Known Antiviral Acyclonucleosides
Buchanan, J. Grant,Craven, David A.,Wightman, Richard H.,Harnden, Michael R.
, p. 195 - 202 (2007/10/02)
Treatment of (S)-4,5-isopropylidenedioxypentanonitrile 17 with ethyl formate and sodium hydride gave a hydroxymethylene derivative which interacted with aminoacetonitrile to give 3-cyanomethyleneamino-2-acrylonitrile 19; this was elaborated via 3-amino-2-cyano-4-pyrrol 22 into 4-amino-7-pyrrolopyrimidine 9.Treatment of the hydroxymethylene derivative of 17 with methanesulphonyl chloride, followed by acetylthioacetonitrile and sodium carbonate in ethanol gave 3-amino-2-cyano-4-thiophene 25, convertible in two steps into 4-amino-7-thienopyrimidine 10. Similar chemistry was employed for the conversion of 5,6-isopropylidenedioxyhexanonitril 30 into the higher homologues 4-amino-7-(3,4-dihydroxybutyl)pyrrolo- and thieno-(3,2-d)pyrimidine 11 and 12, and for the preparation of 4-amino-7-(4-hydroxy-3-hydroxymethylbutyl)pyrrolopyrimidine 13 from 6-benzyloxy-5-benzyloxymethylhexanonitrile 41.The hydroxyalkylated products 9-13 are C-nucleosides analogues of known antiviral agents, but did display antiviral activity.
