Cesium carbonate → tert-Butyl 6-(4-nitrophenoxy)pyrimidin-4-ylcarbamate

Participants

Reaction Steps

A degassed mixture of 4-chloro-6-(4-nitrophenoxy)pyrimidine (WO 2006072589) (1.50 g, 5.96 mmol), tert-butyl carbamate (2.10 g, 17.9 mmol), cesium carbonate (2.91 g, 8.94 mmol), Pd2dba3 (0.218 g, 0.238 mmol) and Xantphos (0.276 g, 0.477 mmol) in DMF was heated at reflux for 1 hr and then maintained at RT for 16 hr. The resulting mixture was partitioned between water (100 mL) and EtOAc (100 mL) and the organic layer was separated and washed with water (2×50 mL) and brine (50 mL) and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in DCM, 0-100%, gradient elution) to afford the title compound as a beige solid (1.22 g, 85% purity, 52%); Rt 4.90 min (Method 1 basic); m/z 331 (M−H)− (ES−).

Provenance & Evidence