Triphenylphosphine → 2-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine

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A solution of Pd(OAc)2 (12 mg, 5 mol %) and PPh3 (52 mg, 20 mol %) in THF (2 mL) was stirred for 5 min, treated dropwise with a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (205 mg, 1 mmol) in THF (1 mL), stirred for 5 min, treated with 5-chlorothiophene-2-boronic acid (244 mg, 1.5 mmol) then saturated aqueous NaHCO3 (1 mL) refluxed for 4 h, cooled, diluted with H2O and filtered to give the title compound (268 mg, 94%) as a grey solid; NMR δH (400 MHz, CDCl3) 7.10 (1H, d, J 4.0 Hz), 7.55 (1H, d, J 5.5 Hz), 7.85 (1H, d, J 4.5 Hz) and 8.08 (1H, d, J 5.5 Hz)

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