Methanol → HCID 69849909, compound

HRID 393155Notes

Reaction equation

HRID 393155 reaction equation
[CH3:1]O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:28])[C:11]([CH2:13][NH:14][CH:15]([C:19]2[C:20]([C:25]([OH:27])=[O:26])=[N:21][CH:22]=[N:23][CH:24]=2)[CH:16]([CH3:18])[CH3:17])=[O:12])=[CH:6][CH:5]=1>S(=O)(=O)(O)O.O>[CH3:1][O:26][C:25]([C:20]1[C:19]([CH:15]([NH:14][CH2:13][C:11](=[O:12])[CH:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[CH3:28])[CH:16]([CH3:18])[CH3:17])=[CH:24][N:23]=[CH:22][N:21]=1)=[O:27]

Participants

5

Reactant 2

HCID 887MethanolHCID 22648753HCID 22648753, compound

Product 1

HCID 69849909HCID 69849909, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A few drops of concentrated sulfuric acid were added to a methanol solution of 2.00 g (5.32 mmol) of 5-(1-{[2-(4-chlorophenyl)-propionyl]methylamino}-2-methylpropyl)-pyrimidine-4-carboxylic acid, followed by heating and refluxing for 5 hours. After completion of the reaction, water was added, followed by extraction with ethyl acetate, and the extract was washed with an aqueous sodium chloride solution, dried over magnesium sulfate and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate) to obtain 0.59 g (yield: 28%) of 5-(1-{[2-(4-chlorophenyl)-propionyl]methylamino}-2-methylpropyl)-pyrimidine-4-carboxylic acid methyl ester (diastereomer A-isomer) as colorless oily product.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 5 hours
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe extract was washed with an aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-4acca31a96a947e587095c89869a174c
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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