Hydrochloric Acid → HCID 21839566, compound

HRID 1738826Notes

Reaction equation

HRID 1738826 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([C:19]4[C:20]5[CH:28]=[CH:27][CH:26]=[N:25][C:21]=5[N:22]=[CH:23][N:24]=4)C(=O)NC(=O)NC3=O)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:19]3[C:20]4[CH:28]=[CH:27][CH:26]=[N:25][C:21]=4[N:22]=[CH:23][N:24]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 54255407HCID 54255407, compound

Product 1

HCID 21839566HCID 21839566, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-(5-indanyl)-5-(pyrido[2,3-d]pyrimidin-4-yl) barbituric acid (3.734 g, 10 mM) and sodium hydroxide (2.00 g, 50 mM) in water (40 ml) is refluxed for 15 h. After cooling the solution is made slightly acidic (pH4-5) by addition of HCl and again refluxed for 15 h. The solution is cooled, made strongly basic with sodium hydroxide and then extracted with ethyl acetate. The organic phase is washed with water, dried and then evaporated to dryness under vacuum. The residue is purified by column chromatography using dichloromethane/methanol 93:7 as eluant. Thus pure title compound is obtained in about 60% yield.

Workup

  1. temperatureAfter cooling the solution
  2. temperatureagain refluxed for 15 h
  3. temperatureThe solution is cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. customdried
  7. customevaporated to dryness under vacuum
  8. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-3edc2e5dfe8c46f1a832f12695423839
Source dataset
uspto-grants-1999_10
Patent number
US05965563

Reaction notes

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