Cesium carbonate → 5-(2,5-Dimethyl-4-nitrophenoxy)pyrimidine

Participants

Reaction Steps

A solution of 1-bromo-2,5-dimethyl-4-nitrobenzene (3.53 g, 15.34 mmol), pyrimidin-5-ol (1.474 g, 15.34 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (0.141 g, 0.767 mmol), cesium carbonate (5.15 g, 15.80 mmol) and copper(I) chloride (0.410 g, 4.14 mmol) in N-methyl-2-pyrrolidinone (15.34 mL) was heated in a sealed pressure tube at 130° C. and stirred overnight. The reaction was cooled to room temperature, diluted with EtOAc and washed with water (2×) and brine, successively, dried over Na2SO4, filtered and concentrated in vacuo. This was triturated with diethyl ether to give the first crop of the desired product (1.682 g) as a light tan solid. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography using an ISCO 80 g column eluting with 0-50% EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give the second crop of the desired product (0.3973 g) as an off-white solid.

Provenance & Evidence