Tetrafluoroborate → (S)-tert-butyl 2-(2-isopropoxy-9H-pyrimido[4,5-b]indol-6-yl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 2-(4-(5-chloro-2-isopropoxypyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate (55 mg, 0.12 mmol), palladium-(II) acetate (2.8 mg, 0.012 mmol), tricyclohexylphopsphine tetrafluoroborate (9 mg, 0.024 mmol) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene; 37 mg, 0.245 mmol) were dissolved in a mixture of o-xylene (0.5 ml) and N,N-dimethylacetamide (0.5 ml). The mixture was degassed with Ar for 5 min, the vessel closed and heated at 155° C. for 16 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The residue was purified by column chromatography (SiO2, 5 to 20% EtOAc in heptane, 2 g ISCO column). White solid (11 mg, 22%). MS (ISP): 413.3 ([M+H]+).

Provenance & Evidence