Sodium Carbonate → HCID 66589040, compound

Participants

Reaction Steps

In a 100 mL microwave vial was placed 3-(2-chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (168 mg, 0.426 mmol) and 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (127 mg, 0.512 mmol) in DME (5 ml) to give a yellow solution. Na2CO3 (2M solution in water) (0.853 ml, 1.706 mmol) was added. The mixture was degassed by bubbling N2 through the solution. Pd(PPh3)4 (49.3 mg, 0.043 mmol) was added. The mixture was heated under reflux (oil bath at 95 C). LC MS (RT 2.8, M+H=481) showed complete conversion after 7.5 h. The reaction mixture was diluted with ethyl acetate and washed with a sat. solution of NaHCO3. A precipitate remained that was insoluble in either organic or aqueous phase. LCMS showed that both the precipitate and the organic phase contained product.

Provenance & Evidence