Hydrochloric Acid → HCID 90410870, compound

Participants

Reaction Conditions

Reaction Steps

5N Aqueous hydrochloric acid solution (0.126 mL, 0.63 mmol) and 20% palladium hydroxide on carbon (0.07 g, 0.50 mmol) were added to a solution of (S)—N2-(5-(1-benzyl-1H-pyrazol-4-yl)-2-methoxypyridin-3-yl)-N4-(1-(5-fluoropyridin-2-yl)ethyl)-5-methylpyrimidine-2,4-diamine (Preparation 9a, 0.214 g, 0.42 mmol) in a 1:1 mixture of methanol/tetrahydrofuran (4 mL) and the reaction mixture was stirred at 50° C. overnight under a hydrogen atmosphere. Further 5N aqueous hydrochloric acid solution (0.126 mL, 0.63 mmol) and palladium catalyst (0.07 g) were then added and the mixture was stirred overnight under a hydrogen atmosphere. The mixture was then filtered through diatomaceous earth (Celite®) and the filter cake was washed with methanol. The combined filtrate and washings were evaporated and a 1:1 mixture of methanol/tetrahydrofuran (4 mL) was added to the residue. 5N aqueous hydrochloric acid solution (0.126 mL, 0.63 mmol) and 20% palladium hydroxide on carbon (0.07 g, 0.50 mmol) were then added to the resulting solution and the reaction mixture was stirred at 50° C. overnight under a hydrogen atmosphere. The mixture was then filtered through Celite® and the filter cake was washed with methanol. The combined filtrate and washings were evaporated to give the title compound (0.166 g, 70%) as a white foam that was used in the next synthetic step without further purification.

Provenance & Evidence