Tetrahydrofuran → HCID 86696591, compound

Participants

Reaction Steps

To a solution of methyl 2-(4-chloro-2-methylpyrimido[1,2-b]indazol-3-yl)acetate (0.289 g; 1 mmol) in dry DMF (4 mL) at −10° C. was slowly added a 1N solution of LHMDS in tetrahydrofuran (1.1 mL; 1.1 mmol). Then, 1-iodopropane (0.146 mL; 1.5 mmol) was added and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was quenched by addition of a saturated solution of ammonium chloride and the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (2-20%) in dichloromethane furnished 0.252 g (76%) of methyl 2-(4-chloro-2-methylpyrimido[1,2-b]indazol-3-yl)pentanoate as an oil. ESI/APCI(+): 332-334 (M+H).

Provenance & Evidence