N-Phenylglycine ethyl ester → HCID 24937863, compound

Participants

Reaction Steps

Ethyl 2-chloro-6-((2-ethoxy-2-oxoethyl)(phenyl)amino)-5-nitropyrimidine-4-carboxylate. A solution of ethyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (1.5 g, 5.67 mmol) in anhydrous tetrahydrofuran (20 mL) was chilled to −78° C. under nitrogen. A solution of ethyl 2-(phenylamino)acetate (1.1 g, 6.22 mmol) and diisopropylethylamine (3.0 mL, 17.01 mmol) in anhydrous tetrahydrofuran (10 mL) was then added dropwise, with stirring, over 10 min. The reaction was stirred at −78° C. for 6 h, followed by addition of aqueous sodium bicarbonate solution (saturated, 10 mL). The mixture was extracted with ethyl acetate (3×10 mL). The organic phase was dried over sodium sulfate and concentrated to a residue which was purified by chromatography on a normal phase silica gel column (0-10% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (1.1 g, 2.89 mmol, 41% yield). MS (ESI) m/z 409.5 [M+1]+.

Provenance & Evidence