Potassium Iodide → HCID 58280079, compound

Participants

Reaction Steps

Heat a mixture of 100 mg (0.25 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-N-piperidin-3-yl-furo[2,3-d]pyrimidin-4-amine (Example 39A), 65 μl (0.375 mmol) of DIEA, 4.1 mg (0.025 mmol) of potassium iodide and 45 mg (0.25 mmol) of 4-bromobutyric acid methyl ester in 2 ml of THF under reflux for 1 h. After cooling, add the reaction mixture to water and extract three times with ethyl acetate. Wash the combined organic phases twice with buffer solution (pH 7) and saturated sodium chloride solution, dry over magnesium sulphate and concentrate under reduced pressure. Purify the crude product by preparative RP-HPLC (eluent: acetonitrile/water gradient), followed by chromatography on silica gel (eluent: dichloromethane→dichloromethane/methanol 50:1). After stirring the resulting product with methanol, the precipitate is filtered off with suction, washed with a little methanol and dried under high vacuum. 58 mg (46.4% of theory) of the target product are isolated.

Provenance & Evidence