Hydrochloric Acid → 4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368990Notes

Reaction equation

HRID 368990 reaction equation
[OH-].[Na+].C([O:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[N:16][C:15](=[O:25])[N:14]([CH2:26][CH3:27])[C:13]=2[N:28]=1)[CH3:8])(=O)C.Cl>CO>[Cl:24][C:20]1[CH:19]=[C:18]([C:17]2[C:12]3[CH:11]=[CH:10][C:9]([CH:7]([OH:6])[CH3:8])=[N:28][C:13]=3[N:14]([CH2:26][CH3:27])[C:15](=[O:25])[N:16]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23284534HCID 23284534, compound

Product 1

HCID 232844934-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-oneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (30 ml) and 30 ml of 1 N sodium hydroxide aqueous solution were added to 6.78 g (18.2 mmol) of 7-(1-acetoxyethyl)-4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one, followed by stirring for 20 minutes at room temperature. The reaction solution was neutralized by adding 1 N hydrochloric acid and extracted with chloroform. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (chloroform) to give 4.50 g of 4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one in the form of crystals. The yield was 75%.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate, magnesium sulfate
  4. customwas removed by filtration
  5. concentrationthe resulting filtrate was concentrated under a reduced pressure
  6. customThereafter, the resulting residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-4d99e4ddd71d4555b5391b4d277b92fe
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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