1,8-Diazabicyclo(5.4.0)undec-7-ene → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid benzyl ester

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (173 mg, contaminated with 10% sulfone, 0.62 mmol) in THF (6 mL) was added benzyl glycolate (128 μL, 0.90 mmol) followed by potassium tert-butoxide (1 M in THF, 0.3 mL, 0.3 mmol) and DBU (139 μL, 0.93 mmol). The solution was stirred for 5 h, diluted with 50% ethyl acetate/hexane, and passed through a plug of SiO2 followed by washing with 40% ethyl acetate/hexane. The filtrate was concentrated in vacuo, and the residue flash-chromatographed on SiO2 with 35% ethyl acetate/hexane to afford 71.5 mg (30% yield) of the titled product as a white solid. ESI-MS m/z 382 (MH+), 380 (M−H)−.

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