Sodium Iodide → 3-(3-Chloro-5-methoxy-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Participants

Reaction Steps

Charge an oven dried flask with 3-(5-bromo-3-chloro-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (0.46 g, 1.1 mmol), copper oxide (0.045 g, 0.56 mmol), sodium iodide (0.020 g, 0.11 mmol), 25% sodium methoxide/methanol solution (10 mL) and anhydrous methanol (10 mL). Reflux the reaction in an oil bath (90° C.) over the weekend under an inert atmosphere. Quench the reaction with ice water and extract with ether (3×100 mL). Combine the organic portions, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue using flash chromatography, eluting with 100% hexane/0% (35% ethyl acetate/hexane) to 0% hexane/100% (35% ethyl acetate/hexane) in a step gradient of 10% increments to give a white foam (0.086 g, 21%). ES/MS m/z (35Cl) 363.7 (M+1)+.

Provenance & Evidence