Hydrochloric Acid → {[1-({[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methoxy}-acetic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Add 0.6 ml of an 11.25N sodium hydroxide solution to a solution of 285 mg (0.68 mmol) of [1-({[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)cyclobutyl]methanol in 5 ml of toluene. After adding 23 mg (0.07 mmol) of tetra-n-butylammonium hydrogensulphate and 267 mg (1.37 mmol) of bromoacetic acid tert-butyl ester, stir the reaction mixture at 70° C. for20 h. After cooling to room temperature, adjust to pH 7 with conc. hydrochloric acid. Extract three times with 20 ml each time of dichloromethane. Wash the combined organic extracts with satd. aqueous sodium chloride solution, dry over sodium sulphate and filter. Concentrate the filtrate under reduced pressure. Purify the crude product by means of preparative RP-HPLC (gradient: water/acetonitrile). 260 mg (72% of theory) of the desired product are obtained.

Provenance & Evidence