Hydrochloric Acid → 2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutan-1-ol

Participants

Reaction Conditions

Reaction Steps

Add 2.7 ml of 11.25 N sodium hydroxide solution to a solution of 1974 mg (14.93 mmol) 2-tert.-butylpropane-1,3-diol in 25 ml toluene, 8 ml 1,2-dimethoxyethane and 8 ml water at 70° C. After adding 101 mg (0.30 mmol) tetra-n-butylammonium hydrogensulphate and 1000 mg (2.99 mmol) 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture for 17 h at 70° C. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract with dichloromethane. Wash the organic phase with satd. sodium chloride solution, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Mix the residue with methanol, filter, and wash with diethyl ether. Purify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile). 275 mg (21% of theor.) of the desired product (racemate) is obtained.

Provenance & Evidence