Ethyl Acetate → {4-[3-(2-Chloro-pyrimidin-4-yloxy)-phenoxymethyl]-benzyl}carbamic acid tert-butyl ester

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Reaction Steps

Under an atmosphere of argon, 3-(2-chloro-pyrimidin-4-yloxy)-phenol (177 mg; 0.8 mmol; Stage 5.1) is dissolved in DMF (4 mL), followed by addition of Cs2CO3 (1.30 g; 4.0 mmol) and stirring is continued for 20 min. (4-Chloromethyl-benzyl) -carbamic acid tert-butyl ester (203 mg; 0.8 mmol) and tetrabutyl ammonium iodide (20 mg) are added, and the reaction is continued for another 1 h 50 min. The reaction mixture is poured onto brine, taken up into EtOAc, washed with water and brine and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure and the crude product is purified by flash chromatography over silica gel (eluting with Hexane/EtOAc 80:20) to give the title compound of Stage 5.2 as an oil; ES-MS: [M+H]+; m/z=442; Rf (Hexane/EtOAc 1:1)=0.50; HPLC: AtRet=5.29 min.

Provenance & Evidence