Hydrochloric Acid → HCID 87617685, compound

Participants

Reaction Steps

A solution of 0.114 g (0.0004 mole) of (rac)-1-(5-amino-2-chloro-pyrimidin-4-yl)-piperidine-3-carboxylic acid ethyl ester (V-67), 1 mL of tetrahydrofuran and 1 mL of 1M sodium hydroxide was stirred at ambient temperature for 3 hours. The mixture was acidified to pH=3 by the addition of 1M hydrochloric acid. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.0812 g of (rac)-1-(5-amino-2-chloro-pyrimidin-4-yl)-piperidine-3-carboxylic acid. This intermediate was stirred with 0.13 g (0.00034 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.058 g (0.00057 mol) of triethylamine and 2 mL of dichloromethane overnight at ambient temperature. The mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.075 g of (rac)-4-chloro-1,3,5,8-tetraaza-tricyclo[8.3.1.0*2,7*]tetradeca-2,4,6-trien-9-one (VI-67).

Provenance & Evidence