Sodium Hydroxide → HCID 10250660, compound

HRID 703449Notes

Reaction equation

HRID 703449 reaction equation
[O:1]=[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29].[OH-].[Na+]>CO>[O:1]=[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:4][N:3]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10251460HCID 10251460, compound

Product 1

HCID 10250660HCID 10250660, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-oxo-4,5-diphenyl-1(2H)-pyrimidinenonanoate (4.70 g, 11 mmol), 5N NaOH solution (7.40 mL, 36 mmol) and methanol (80 mL) was stirred at room temperature for 75 minutes and than at reflux for 75 minutes before being cooled and concentrated. The residue was diluted with water and 2N HCl was added until pH=2. The mixture was extracted with CH2Cl2, the extracts combined, dried over sodium sulfate and the solvent evaporated to leave an oil that crystallized. Recrystallization from a mixture of diethyl ether and CH2Cl2 afforded 2-oxo-4,5-diphenyl-1(2H)-pyrimidinenonanoic acid (3.35 g, 73%), m.p. 120°-123° C.

Workup

  1. temperaturethan at reflux for 75 minutes
  2. temperaturebefore being cooled
  3. concentrationconcentrated
  4. additionThe residue was diluted with water and 2N HCl
  5. additionwas added until pH=2
  6. extractionThe mixture was extracted with CH2Cl2
  7. dry with materialdried over sodium sulfate
  8. customthe solvent evaporated
  9. customto leave an oil
  10. customthat crystallized
  11. customRecrystallization
  12. additionfrom a mixture of diethyl ether and CH2Cl2

Sources & evidence

ORD record
ord-0aa9aced69c143429469a79b26ec0bff
Source dataset
uspto-grants-1991_01
Patent number
US04983610

Reaction notes

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