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

HRID 417827Notes

Reaction equation

HRID 417827 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([O:14]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:10]2)[C:4](=[O:26])[N:3]=1.C[O-].[Na+]>>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)[C:4](=[O:26])[N:3]=1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 666491404-nitro-benzoic acid 3-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester

Product 1

HCID 666491684-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-oneYield 46.4%

Procedure

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%).

Workup

  1. customthe solvent was removed in vacuo
  2. filtrationpurified by silica gel plug filtration (20 g SiO2, CH2Cl2/Methanol/ammonium hydroxide: 88/12/0.25)

Sources & evidence

ORD record
ord-fce38d31686147b7a34d952723f68105
Source dataset
uspto-grants-2012_01
Patent number
US08093245B2

Reaction notes

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