Hydrochloric Acid → trans-({3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexyl}oxy)acetic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Add a solution of 625 mg (1.606 mmol) of cis/trans-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexanol in 3 ml of toluene to a mixture of 2 ml of toluene and 1.28 g of 50% sodium hydroxide solution (16.05 mmol). Then add 54.5 mg (0.16 mmol) of tetra-n-butylammonium hydrogen sulphate and 626 mg (3.21 mmol) of bromoacetic acid tert-butyl ester to the biphasic mixture, and stir the reaction mixture vigorously at 60° C. for 3 h. Then add to water and neutralize with conc. hydrochloric acid. Extract the aqueous phase three times with ethyl acetate, combine the organic phases and dry over magnesium sulphate. The residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1→8:1). 592 mg of the target compound are obtained (73.2% of theory).

Provenance & Evidence