Sodium Hydroxide → HCID 18326601, compound

HRID 1250701Notes

Reaction equation

HRID 1250701 reaction equation
C[O:2][C:3]([C:5]1[CH:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[CH:13]=2)[NH:7][C:8](=[O:11])[NH:9][CH:10]=1)=[O:4].[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>CO>[F:19][C:14]1[CH:13]=[C:12]([CH:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:10][NH:9][C:8](=[O:11])[NH:7]2)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 10730591HCID 10730591, compound

Product 1

HCID 18326601HCID 18326601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (−)-4-(3,4-Difluorophenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester (450 mg, 1.68 mmol) in 15 mL MeOH was added 1M NaOH (28 mL, 28.0 mmol). The solution was stirred under argon at room temperature for 6 h, poured 10% potassium hydrogen sulfate, and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo to give the product. 1H NMR dH (DMSO) 9.17 (d, 1H, J=5.37Hz), 7.69 (s, 1H), 7.50-7.35 (m, 1H), 7.30-7.20 (m, 2H), 7.15-7.05 (m, 1H), 5.13 (d, 1H, J 2.44).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-7afdc19d91d2462299cd790bae1e7245
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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