Triethylamine → 4-Phenyl-6-phenylethynylpyrimidin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-phenylpyrimidin-2-ylamine (2.0 g, 9.7 mmol), (PPh3)2PdCl2 (204 mg, 0.29 mmol), triethylamine (4.9 g, 48.5 mmol) in DMF (10 mL) was stirred at 25° C. for 0.5 hour under a nitrogen atmosphere. Then phenylacetylene (1.29 g, 12.70 mmol) was added to it and the mixture was stirred at 100° C. for 4 hours under a nitrogen atmosphere. The mixture was cooled to temperature in the range of 20-40° C., diluted with water (20 mL) and extracted with EtOAc (3×25 mL). The organic layers were collected, combined, washed with water (30 mL), dried over anhydrous Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography using EtOAc-petroleum ether to give the desired product.

Provenance & Evidence