N,N,N',N'-Tetramethylethylenediamine → HCID 46701122, compound

Participants

Reaction Conditions

Reaction Steps

4-[7-(6-chloro-5-fluoropyridin-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (186 mg, 0.410 mmol, Example 6), Zinc cyanide (57 mg, 0.48 mmol), N,N,N′,N′-tetramethylethylenediamine (86 μL, 0.57 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg, 0.018 mmol, Alfa Aesar Cat. No. 12760) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (30 mg, 0.053 mmol) (Aldrich, Cat. No. 526460) were added successively to N-Methylpyrrolidinone (5 mL) in a microwave tube. The tube was sealed and degassed with nitrogen and heated at 160° C. overnight. The reaction mixture was cooled to r.t. and filtered. The filtration was diluted with MeOH and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS (M+H)+: m/z=445.3.

Provenance & Evidence