Sodium Hydroxide → 1-(3,4-Difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

HRID 1038971Notes

Reaction equation

HRID 1038971 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]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58443073HCID 58443073, compound

Product 1

HCID 584430401-(3,4-Difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue, water (5 mL) and ethyl acetate (2.5 mL) were added
  3. washThe aqueous layer was washed with ethyl acetate
  4. extractionThe aqueous layer was then extracted with ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1632a5fd99a49ad8157f905f5f57538
Source dataset
uspto-grants-2013_10
Patent number
US08552019B2

Reaction notes

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