Water → methyl 5-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-chloroimidazo[1,2-c]pyrimidine-7-carboxylate (1.00 g, 4.73 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (Preparation E; 1.53 g, 4.73 mmol), K3PO4 (2.01 g, 9.45 mmol), Pd2dba3 (0.433 g, 0.473 mmol), and XPHOS (0.563 g, 1.18 mmol) were combined dry. To this was added isopropanol (20 mL) and water (0.34 mL, 19 mmol). After de-gassing for 10 minutes, the flask was sealed and heated to 80° C. for 15 hours. The reaction mixture was diluted in EtOAc and undissolved solid was removed by filtration. The filtrate was concentrated down and purified by silica chromatography using 50-100% EtOAc/Hexanes gradient to afford methyl 5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (0.477 g, 1.28 mmol, 27.0% yield) as an orange brown solid. MS (apci) m/z=374.1 (M+H).

Provenance & Evidence