Diisoamylamine → HCID 68277118, compound

Participants

Reaction Steps

To a solution of 2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylic acid in DMF (10 mL) and methylene chloride (5 mL) was added diisopentylamine (0.67 mL; 512 mg; 3.3 mmol) and hydroxybenzotriazole monohydrate (499 mg; 3.3 mmol). The mixture was stirred for 10 min. at room temperature and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (626 mg; 3.3 mmol) was added. The mixture was stirred overnight at room temperature. An additional amount of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride was then added (626 mg; 3.3 mmol) and the reaction mixture was heated to 50° C. for 30 min. The mixture was then cooled to room temperature, diluted with methylene chloride and saturated ammonium chloride was added. The aqueous layer was back extracted with methylene chloride and the combined organics were washed with water (3×10 mL) and brine. Concentration afforded a crude oil that was purified by flash-chromatography using first 100% methylene chloride then 5% methanol in methylene chloride to afford an oil that solidified under vacuum. This solid was taken into hot methanol (7 mL) and, upon cooling, a solid formed. Water (3 mL) was then added slowly and filtration afforded 590 mg (89%) of the title compound. LCMS m/z 409.3 (M+H)+, ret. time=3.08 min.

Provenance & Evidence