Dimethylformamide → HCID 86712719, compound

Participants

Reaction Steps

10% Pd/C (53% water; 0.020 g) was added to a solution of methyl 2-(2-((5-methyl-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-ylethynyl)phenyl)acetate (A115) (0.115 g, 0.318 mmol) in DMF (5 mL) and Et3N (0.5 mL) and the resulting suspension placed under a hydrogen atmosphere and stirred at room temperature for 18 hours. The mixture was filtered through Celite, washing with EtOAc (250 mL). The combined filtrates were washed with water (100 mL) then brine (100 mL) and the washing repeated 3 times. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure and the resulting oil purified by silica gel column chromatography (Biotage Isolera, 24 g SiO2 cartridge, 0-100% EtOAc in hexanes) to give the title compound A116 as a yellow solid (0.097 g, 83%); 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.83 (s, 1H), 7.46 (s, 1H), 7.25-7.17 (m, 4H), 6.75 (s, 1H), 3.89 (s, 3H), 3.72 (s, 2H), 3.67 (s, 3H), 3.09 (dd, J=9.5, 6.3 Hz, 2H), 2.91 (dd, J=9.5, 6.4 Hz, 2H), 2.07 (s, 3H). LCMS-A: rt 5.160 min; m/z 366 [M+H]+.

Provenance & Evidence