Amino-thienopyrimidine Series

This experiment uses slightly different conditions to those already tested in a Suzuki coupling that will hopefully generate the aminothienopyrimidine hit.

Conclusion: Thienopyrimidine series hit compound sythesised. Accurate yield not obtained. Current stock = 12.8 mg.

Experiment start time: 2pm, 26/11/2012 6-bromothieno[3,2-d]pyrimidin-4-amine (34.6 mg, 0.15 mmol, 1 eq), 3-sulfamoylphenylboronic acid, pinacol ester (46.7 mg, 0.16 mmol, 1.1 eq) and potassium acetate (59.3 mg, 0.6 mmol, 4 eq) were dissolved in 20% 1,4-dioxane/H2O and degassed for 2 hr with nitrogen gas. To the degassed solution was added PdCl2(dppf) (10 mg, 10 mol%). The resultant solution was heated at reflux for 23 hr. The solution was allowed to cool to rt. Product extracted with EtOAc (30 mL). Washed with water (2 x 20 mL), brine (20 mL), dried over MgSO4 and concentrated in vacuoto yield an orange solid. Purified via recrystallisation from 50% EtOH/H2O to yield orange crystals (12.8 mg, 0.04 mmol, 28%).*

*Yield not accurate. This number refers to current stock only.

Low res mass spec.: 634.53 ([2M+Na]+)

¹H-NMR (200 MHz):

¹H-NMR (300 MHz):

¹³C-NMR (300 MHz):