Sodium Hydroxide → 1-(3,4-Difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][N:6]1[C:11](=[O:12])[C:10]([C:13]([O:15]CC)=[O:14])=[CH:9][N:8]=[CH:7]1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[F:21])[CH2:5][N:6]1[C:11](=[O:12])[C:10]([C:13]([OH:15])=[O:14])=[CH:9][N:8]=[CH:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 1-(3,4-difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate (470 mg, 1.597 mmol) in methanol (3195 μl) at 0° C., aqueous sodium hydroxide (1917 μl, 1.917 mmol, 1M) was added dropwise. After warming to room temperature over 2 h, the reaction mixture was concentrated under reduced pressure. To the residue, water (5 mL) and ethyl acetate (2.5 mL) were added. The aqueous layer was washed with ethyl acetate and then acidified to pH 1 with aqueous hydrochloric acid (1M). The aqueous layer was then extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 1-(3,4-difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid as a white solid. LRMS (ESI) calc'd for (C12H9F2N2O3) [M+H]+, 267.1; found 267.0.