Potassium Phosphate, Tribasic → 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrrol-3-yl)imidazo[1,2-c]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 5-chloro-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation J; 0.150 g, 0.642 mmol), 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid (0.257 g, 0.963 mmol), and potassium phosphate (0.321 mL, 0.642 mmol) was added 6 mL of dioxane and argon was bubbled through the mixture for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.0742 g, 0.0642 mmol) was added and argon was bubbled through the reaction for 15 minutes. The flask was sealed under argon and the mixture was heated at 75° C. with stirring overnight. The reaction was then concentrated under reduced pressure and then taken up in DCM (5 mL). A precipitate was formed and collected by means of vacuum filtration and washed with DCM (10 mL). The solid contained product without the triisopropylsilyl protection as well as inorganic salts. Further purification was not attempted and so was obtained 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrrol-3-yl)imidazo[1,2-c]pyrimidine (0.220 g, 0.832 mmol, 130% yield). MS (apci) m/z=265.1 (M+H).

Provenance & Evidence