2-Bromopyridine → 7H-Pyrrolo[2,3-d]pyrimidine, 2-chloro-5-methyl-7-(2-pyridinyl)-

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-Chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (80 mg, 0.48 mmol), 2-bromopyridine (113 mg, 0.72 mmol), copper(I) iodide (9.1 mg, 0.48 mmol), K3PO4 (2.02 g, 23.84 mmol), and trans-1,2-diaminocyclohexane (5.44 mg, 0.48 mmol) in 1,4-dioxane (7 mL) is stirred at 90° C. for 1.5 hrs. After cooling to room temperature the reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (anhydrous Na2SO4) and the solvent is evaporated. The crude product is purified by flash chromatography (gradient elution ethyl acetate:heptanes 0:1 to 1:4) on silicagel to afford 2-Chloro-5-methyl-7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine as a white solid (55%).

Provenance & Evidence