Water → HCID 59506448, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution at 0° C. of diisopropylamine (51.0 mL, 0.361 mol) in tetrahydrofuran (600 mL) was added n-BuLi (221 mL, 0.353 mol, 1.6 M in hexane) dropwise and the mixture was stirred at the 0° C. for 45 min. The reaction mixture was then cooled to −78° C. and a solution of ethyl 4-(benzyl(3-ethoxy-3-oxopropyl)amino)-6-chloro-2-(methylthio)pyrimidine-5-carboxylate (50 g, 0.114 mol) in tetrahydrofuran (500 mL) was added drop wise over 45 min. The reaction mixture was stirred at -78° C. for 15 min before water (1 L) was added. The reaction mixture was then warmed to room temperature and the organic phase was separated from the aqueous layer. The aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with water (1 L), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude ethyl 8-benzyl-4-chloro-2-(methylthio)-5-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-carboxylate that was used for next step directly.

Provenance & Evidence