Sodium Hydroxide → HCID 178503325, compound

Participants

Reaction Conditions

Reaction Steps

Crude ethyl 4-hydrazinyl-2-(methylthio)-5-oxo-8-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate (20 g), was dissolved in ethanol (300 mL). Aqueous sodium hydroxide (300 mL) (22.52 g, 563 mmol) was added. The reaction mixture was warmed to 60° C. and stirred for 3 h. Upon completion of the reaction (TLC, LCMS), ethanol was removed under reduced pressure and the aqueous layer was acidified using 10% citric acid. The aqueous layer was then extracted with dichloromethane (200 mL×3). The combined organic layers were washed with water (500 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give crude 7-(methylthio)-5-phenyl-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene-3-carboxylic acid (20 g). The crude product was used for decarboxylation in the next step without purification. LCMS [M+H]: 328

Provenance & Evidence