Acetic Acid → {2-[3'-(2-Cyano-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester

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Reaction Steps

A mixture of {2-[3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester (150 mg), potassium cyanide (76 mg) and 1,4-diazabicyclo[2,2,2]octane (13 mg) in water (0.4 ml) and DMSO (2 ml) is left at 5° C. for 4 h. This mixture is acidified with AcOH to pH 4-5, quenched with brine and extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1 to afford pure {2-[3′-(2-cyano-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester.

Provenance & Evidence