4-Nitrobenzoic Acid → 4-nitro-benzoic acid 3-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester

HRID 417826Notes

Reaction equation

HRID 417826 reaction equation
[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:15])[N:3]=1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>>[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:23](=[O:24])[C:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:27][CH:26]=3)[CH2:10]2)[C:4](=[O:15])[N:3]=1

Participants

3

Reactant 2

HCID 61084-Nitrobenzoic AcidHCID 666491684-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one

Product 1

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

Procedure

4-Amino-5-fluoro-1-(3-hydroxy-cyclopentyl)-1H-pyrimidin-2-one was inverted via the Mitsunobu reaction (General Method A) with 4-nitrobenzoic acid to provide 4-nitro-benzoic acid 3-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-cyclopentyl ester 28.

Sources & evidence

ORD record
ord-c55f5a1f4f3c42ff91daa1ab18bf7fc8
Source dataset
uspto-grants-2012_01
Patent number
US08093245B2

Reaction notes

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