Cesium carbonate → 3-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methylene)azetidine-1-carboxylate (0.88 g, 2.9 mmol), 2-ethylbenzimidazole (0.40 g, 2.74 mmol), Xphos (0.10 g, 0.21 mmol), Pd2(dba)3 (0.10 g, 0.11 mmol) and cesium carbonate (1.4 g, 4.2 mmol) in DMF (4.0 mL) was heated in a Biotage microwave at 140° C. for 30 minutes. The reaction mixture was then filtered through paper and then partitioned between brine and EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (0-10% MeOH in DCM) to give the title compound (1.2 g, quant.). LCMS m/z: 531.2 (MH+).

Provenance & Evidence