Hydrochloric Acid → trans-3-[(5-Bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]cyclohexanol

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Reaction Conditions

Reaction Steps

Dissolve 1.1 g (8.88 mmol) of cis/trans-cyclohexanediol at 70° C. in 10 ml of toluene and 5 ml of 1,2-dimethoxyethane and add 2.84 g of 50% sodium hydroxide solution (35.5 mmol). Add water until a biphasic reaction mixture forms. Add 120.6 mg (3.55 mmol) of tetra-n-butylammonium hydrogen sulphate and 1.10 g (3.55 mmol) of 5-bromo-4-chloro-6-phenylfuro[2,3-d]pyrimidine, and stir the mixture vigorously at 70° C. for 1 h. After cooling, add the reaction mixture to water and neutralize with conc. hydrochloric acid. Extract the aqueous phase three times with ethyl acetate. Combine the organic phases, wash with satd. sodium hydrogen sulphate solution, dry over magnesium sulphate and concentrate under reduced pressure. Purify the residue by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→3:1). 0.63 g of the title compound is obtained (45.6% of theory).

Provenance & Evidence