Amino-thienopyrimidine Series

 

This experiment is a Suzuki coupling to form a derivative within the thienopyrimidine series. Conclusion: Desired product not synthesised. Homocoupled product looks to have been isolated by HNMR and low res. mass spec. Experiment start time: 9:45 am, 13/12/20126-bromothieno[3,2-d]pyrimidin-4-amine (49 mg, 0.21 mmol, 1 eq), phenylboronic acid (36 mg, 0.30 mmol, 1.4 eq), dried potassium acetate (108.5 mg, 1.105 mmol, 5.3 eq) and PdCl2(dppf) (7.1 mg, 4.2 mol %) were dissolved in 1,4-dioxane/water (5:1, 5 mL). The solution was stirred whilst heated to reflux for 72 h. Crude yield = 38 mg. Multiple products present by TLC (EtOAc: rf = 0.4, 0.5, 0.7, 0.8, 0.9). Difficult column will be necessary. Column performed using 10% EtOAc/hex -> 100% EtOAc. One product eluted (8 mg). This product has an 1H-NMR spectrum consistent with the desired product, though the fairly complex aromatic region means that multiplicity could not be determined. SPECTRUM NEEDS TO BE UPLOADED. low res mass spec shows weight consistent with homocoupled thieno[3,2-d]pyrimidine.