Citric Acid → (3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propoxy)acetic acid

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Reaction Conditions

Reaction Steps

Put 200 mg (0.53 mmol) 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propan-1-ol with 518 mg (2.66 mmol) bromoacetic acid tert.-butyl ester and 36 mg (0.106 mmol) tetra-n-butylammonium hydrogensulphate in 5 ml dichloromethane and cool to 0° C. Add 1.0 ml 50% sodium hydroxide solution and stir vigorously at 0° C. Then leave to return to RT and continue stirring vigorously overnight. Then dilute with dichloromethane and water, acidify with 10% citric acid solution and separate the phases. Re-extract the aqueous phase once with dichloromethane. Combine the organic phases, wash once with satd. sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. Dissolve the residue in 5 ml dichloromethane. Add 1.25 ml TFA and stir for 2 h at RT. Then concentrate by evaporation and dry at high vacuum. Purify the residue chromatographically on a silica-gel thick-layer plate (solvent: dichloromethane/methanol 95:5). Extract the product zone with dichloromethane/methanol 9:1. 50 mg (23.0% of theor.) of the target compound is obtained.

Provenance & Evidence