Sodium Carbonate → tert-Butyl 6-[2-(cyclopropyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Reaction Conditions

Reaction Steps

A 4:1 mixture (0.097 g, 0.27 mmol) of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, 5-bromo-2-cyclopropylpyrimidine (0.054 g, 0.27 mmol), PdCl2×dppf (0.0045 g), 2M sodium carbonate (1.0 mL), toluene (4.0 mL) and EtOH (1.0 mL) was purged with dry argon for ten minutes, then heated in a sealed vial at 81° C. for 6 h. The black solution was filtered through glass-wool, taken up in water-brine and washed twice with EtOAc. The combined organic phases were dried, filtered and concentrated with silica (5 g). Column chromatography with EtOAc-heptanes (1:5 through 1:2) gave 0.034 g (36%) of the title product as white solid.

Provenance & Evidence