Water → (2R)-N-Benzyl-2-{[5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-N-methylpropane-1-amine

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Reaction Steps

Add 167 mg (4.18 mmol) sodium hydride (as 60% dispersion in mineral oil) to a solution of 600 mg (3.35 mmol) (2R)-1-[benzyl(methyl)amino]propan-2-ol in 7 ml THF at room temperature. After stirring for ten minutes, add a solution of 1177 mg (3.51 mmol) 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine in 8 ml THF and 62 mg (0.17 mmol) tetra-n-butylammonium iodide. Stir the reaction mixture for 16 h under reflux. After adding water and ethyl acetate, wash the separated organic phase with 1 N hydrochloric acid and satd. sodium chloride solution. Re-extract the aqueous phase with ethyl acetate. Combine the organic phases and dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Take up the residue in cyclohexane/ethyl acetate/dichloromethane and chromatograph on silica gel (solvent: cyclohexane/ethyl acetate 5:1, 2:1, 1:1, then ethyl acetate). 1366 mg (83% of theor.) of the desired product is obtained.

Provenance & Evidence