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12th December 2012 @ 22:48

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.


low res mass spec shows weight consistent with homocoupled thieno[3,2-d]pyrimidine.

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