Sodium Carbonate → HCID 68752963, compound

Participants

Reaction Conditions

Reaction Steps

N—((S)-1-(8-chloro-1-(4-methylpiperazin-1-yl)isoquinolin-3-yl)ethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 140 (80 mg, 0.16 mmol, 1.0 eq), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (66 mg, 0.32 mmol, 2.0 eq), PdCl2(dppf) (13 mg, 0.016 mmol, 0.1 eq) and Na2CO3 (84 mg, 0.79 mmol, 5.0 eq) were suspended in a mixture of N,N-dimethylacetamide (5 mL) and water (2 mL). The resulting mixture was degassed and back-filled with argon three times and then stirred at 80° C. under argon overnight. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM) to afford the product, N—((S)-1-(8-(1-methyl-1H-pyrazol-4-yl)-1-(4-methylpiperazin-1-yl)isoquinolin-3-yl)ethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 141.

Provenance & Evidence