Hydrochloric Acid → 3-{[5-(4-Ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]oxy}cyclohexanol

Participants

Reaction Conditions

Reaction Steps

Add 4.5 ml of 12.5N sodium hydroxide solution at 70° C. to a mixture of 1.65 g (14.17 mmol) of cyclohexane-1,3-diol in 45 ml of toluene, 15 ml of 1,2-dimethoxyethane and 15 ml of water. After adding 0.19 g (0.57 mmol) of tetra-n-butylammonium hydrogen sulfate and 2.0 g (5.67 mmol) of 4-chloro-5-(4-ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidine, stir the reaction mixture at 70° C. for 17 hours. After cooling to room temperature, adjust to pH 7 with conc. hydrochloric acid. Extract with dichloromethane. Wash the organic phase with satd. sodium chloride solution, dry over sodium sulphate, filter and concentrate under reduced pressure. Chromatograph the residue on silica gel (eluent: cyclohexane/ethyl acetate 2:1). 0.60 g (24% of theory) of the desired product are obtained as a racemic diastereomer mixture.

Provenance & Evidence