Amino-thienopyrimidine Series

 

Repeat of AT-6-2 at a greater concentration (i.e. use of more substrate). To AT-5 (0.200 g, 0.80 mmol, 1.0 equiv.) in a sealed tube was added ammonia:propanol (1:1, 8 mL)  and the reaction mixture stirred at 120 C. The reaction was monitored by TLC.  Reaction was cooled to rt after 6 hours, after no apparent change was observed by TLC analysis. The volatiles were removed under reduced pressure and the residue purified by flash column chromatography (95:4.5:0.5 dichloromethane:methanol:ammonia) to give starting material AT-5 (0.141 g, 71%) and product AT-6 (0.039 g, 21% or 72% based on RSM).  HIRAC [data]5684[/data] NMR [data]5723[/data] 1H NMR spectrum of recovered starting material AT-5. [data]5721[/data] 1H NMR spectrum of product AT-6.