Potassium Carbonate → 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-chloro-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation J, 132 mg, 0.565 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (164 mg, 0.847 mmol) in DME (4 mL) was added 1M K2CO3 (1.69 mL, 1.69 mmol) and the resulting solution was purged with N2 for 15 minutes. Pd(PPh3)4 (65.3 mg, 0.0565 mmol) was added, the flask sealed, and the mixture stirred at 90° C. for 15 hours. The reaction mixture was cooled to ambient temperature and diluted with H2O (10 mL). The aqueous mixture was extracted with EtOAc, the extracts were combined and diluted with hexanes (1 vol). After standing for 15 minutes, the resulting precipitate was collected by vacuum filtration and washed with 50% EtOAc-hexanes to afford desired product. The EtOAc filtrate was extracted with 1M NaOH and the extracts were combined with the previous aqueous portion. The aqueous mixture was treated with 6M HCl to pH 4 then with NaCl to saturation. The mixture was extracted with DCM and the combined extracts were dried over Na2SO4, filtered through a Celite pad and concentrated. The residual product was combined with the previous batch and dried in vacuum to provide the title compound (133 mg, 89% yield) as a light yellow solid. MS (apci) m/z=266.2 (M+H).

Provenance & Evidence