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3rd April 2013 @ 01:48

Synthesis of the hydrazine-substituted thienopyrimidine. Following conditions loosely based on Russian Journal of Applied Chemistry200578, 3, 465.

 

To AT-5 (0.100 g, 0.40 mmol, 1.0 equiv.) in isopropanol (5 mL) was added hydrazine hydrate (0.125 mL, 4.0  mmol, 10 equiv.). The reaction mixture was stirred at 60 C and monitored by TLC. 

Reaction judged to be complete by TLC at 5 hours, with complete disappearance of starting material and appearance of a compound of similarity polarity to the similarly substituted aminothienopyrimidine (AT-6). The reaction mixture was diluted with water (10 mL) and extracted into ethyl acetate (3 x 30 mL). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure and the residue purified by flash column chromatography (95:4.5:0.5 dichloromethane:methanol:ammonia) to give a yellow solid. 

HIRAC

AT-18-1.pdf

 

NMR

AT-18-1.pdf
1H NMR (400 MHz, MeOD) of isolated material. Signals not coincident with those of AT-6, i.e. this is not the amino-substituted product, consistent with desired hydrazyl-substituted product.
Attached Files
AT-18-1.pdf
AT-18-1.jpg
AT-18-1.pdf