Sodium hydride → tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate

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Under an atmosphere of argon and at 0 C, 26 mg of trans-2-fluorocyclohexanol were added to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min, a solution of 100 mg of tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature, the mixture was quenched by addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure. This gave 101 mg of the title compound.

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