Propyne → HCID 22027559, compound

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Reaction Steps

Using a high pressure tube, propyne (5 mL) was condensed in a mixture of 2,4-dichloro-pyrimidine (1.71 g, 11.47 mmol), CuI (228 mg, 1.20 mmol), Pd(PPh3)2Cl2 (0.57 mmol), and Et3N (50 mL) at −78° C. The mixture was slowly warmed up and stirred at room temperature for 12 h. After this period, the mixture was quenched with aqueous NH4Cl. The aqueous phase was thoroughly extracted with hexanes. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4; and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 5%-15% EtOAc/hexanes to give 19 (1.64 g, 94%).

Provenance & Evidence