Sodium Methoxide → 4-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one

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Reaction Steps

A solution of 4-Nitro-benzoic acid 3-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester (1.27 g, 3.50 mmol) in anhydrous sodium methoxide (0.5 M in methanol, 20 mL, 10 mmol). The mixture was stirred under nitrogen at room temperature for 2 hours, and the solvent was removed in vacuo. The residue was dry-loaded onto silica gel and purified by silica gel plug filtration (20 g SiO2, CH2Cl2/Methanol/ammonium hydroxide: 88/12/0.25) to afford 4-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one 29 as an off-white solid (0.346 g, 46%).

Provenance & Evidence