Potassium Carbonate → N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine

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Reaction Steps

4-(3-aminopropyl)aniline (0.034 g, 0.23 mmol) was added to a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (0.04 g, 0.15 mmol), copper(I) iodide (0.009 g, 0.04 mmol) and potassium carbonate (0.0626 g, 0.453 mmol) in N,N-dimethylacetamide (3 mL) and the resulting mixture was subjected to microwave radiation at 140° C. for 4 hours. The solvent was then removed by evaporation, and the residue was dissolved in ethyl acetate (50 mL), filtered, and the organics were washed with a saturated solution of sodium bicarbonate (30 mL). Concentration and purification by silica gel column chromatography (using 1-3% methanol, 0.06% ammonia in 1:1 ethyl acetate/hexane) afforded N-[3-(4-aminophenyl)propyl]-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine as a white solid in 30% yield.

Provenance & Evidence