Diethyl Malonate → 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid diethyl ester

Participants

Reaction Steps

A solution of diethyl malonate (0.704 mL, 4.64 mmol) in DMF (2 mL) was added dropwise to a suspention of NaH (200 mg, 4.64 mmol, 55% in mineral oil) in DMF (4 mL) at 0° C. under argon. The reaction mixture was stirred for 30 min and a solution of 5-bromomethyl-2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin (1.5 g, 3.86 mmol) in DMF (4 mL) was added dropwise. The mixture was stirred at room temperature for 3 h. EtOAc was added and the solution was washed with water and brine, dried and concentrated under reduced pressure. Flash chromatography (heptane/EtOAc, 3:2) gave 2-(2-[N,N-bis(tert-butoxycarbonyl)amino]-pyrimidin-5-ylmethyl)-malonic acid diethyl ester (0.87 g, 40%).

Provenance & Evidence