Dimethylamine, hydrochloride → Ammonia methanol

Participants

Reaction Conditions

Reaction Steps

Alternatively, a heterogeneous mixture of 3-(3-(dimethylamino)prop-2-en-1-onyl)-6-chloropyridine (0.063 g, 0.75 mmol) and [3-methyl-4-((1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-5-yl)phenyl]guanidine TFA salt (0.110 g, 0.75 mmol) with K2CO3 (0.051 g, 2.25 mmol) in isopropanol (1 mL) was shaken in a sealed tube at 100° C. in for 24 h. The formation of 4-(6-(chloro)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine was confirmed by LCMS. To this reaction vial 40% of aqueous solution of Me2NH.HCl solution (1 mL) was added and then heated in a sealed tube for 3 h at 100° C. The resulting reaction mixture was purified by column chromatography (silica gel; CH2Cl2 then 1% 2N NH3/MeOH in CH2Cl2) to afford 4-(6-(N,N-dimethylamino)pyridin-3-yl)-N-(3-methyl-4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)pyrimidin-2-amine, compound #1; LCMS: purity: 99%; MS (m/e): 416 (MH+).

Provenance & Evidence