tert-Butyl ethyl malonate → HCID 57976104, compound

Participants

Reaction Steps

To 1-(2-methoxy-ethyl)-piperidin-4-ylamine (4, 1.7 g, 11 mmol) in EtOH (20 mls) was added a solution of the 1:1 mixture of 2-(2-chloro-5-nitro-pyrimidin-4-yl)-malonic acid tert-butyl ester ethyl ester (3) and tert-butyl ethyl malonate (2) (˜5.3 mmol of 3) in EtOH (20 mls) dropwise with stirring. The resulting mixture was stirred at room temperature overnight and then diluted with EtOAc, washed with H2O (1×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo. The resulting residue was purified by flash chromatography (eluting solvents=CH2Cl2, followed by 2% MeOH in CH2Cl2, followed by 4% MeOH in CH2Cl2) to give 2-{2-[1-(2-methoxy-ethyl)-piperidin-4-ylamino]-5-nitro-pyrimidin-4-yl}-malonic acid tert-butyl ester ethyl ester (5, 733 mgs, 29%). LC/MS Calcd for [M+H]+ 468, found 468.

Provenance & Evidence