4-Amino-2-chloro-6-methyl-5-nitropyrimidine → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-5-nitropyrimidin-4-amine

Participants

Reaction Steps

Under argon, 1.50 g (4.25 mmol) of the compound from Example 33A were initially charged in 1,4-dioxane (37.5 ml), and the reaction mixture was purged with argon for 10 min. Thereafter, 3.22 ml (6.37 mmol) of hexabutylditin and 881 mg (4.67 mmol) of 2-chloro-6-methyl-5-nitropyrimidin-4-amine were added. Subsequently, 1.49 g (2.12 mmol) of bis(triphenylphosphine)palladium(II) chloride were added and the reaction mixture was heated to reflux overnight. Thereafter, the mixture was cooled to RT and filtered through Celite, and the filtrate was washed through with methanol. The solids formed were filtered off and discarded. The remaining filtrate was concentrated, ethyl acetate was added, and the solids formed were filtered off and dried under high vacuum. This gave 640 mg (69% purity, 27% of theory) of the title compound. The crude product was converted further without further purification.

Provenance & Evidence