Hydrochloric Acid → HCID 12151361, compound

HRID 393149Notes

Reaction equation

HRID 393149 reaction equation
C([O:3][CH:4](OCC)[C:5]1[C:10]([CH:11]([N:15]([CH3:26])[C:16](=[O:25])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:12]([CH3:14])[CH3:13])=[CH:9][N:8]=[CH:7][N:6]=1)C.Cl>CC(C)=O>[CH:4]([C:5]1[C:10]([CH:11]([N:15]([CH3:26])[C:16](=[O:25])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:12]([CH3:13])[CH3:14])=[CH:9][N:8]=[CH:7][N:6]=1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12151360HCID 12151360, compound

Product 1

HCID 12151361HCID 12151361, compoundYield 766.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8.4 g (2.1 mmol) of N-[1-(4-diethoxymethylpyrimidin-5-yl)-2-methylpropyl]-N-methy4-fluorophenylacetamide was dissolved in 100 ml of acetone, and 13 ml of 6N hydrochloric acid was added and reacted at room temperature for 5 hours. After completion of the reaction, the reaction solution was concentrated, and an aqueous sodium hydrogencarbonate solution was added to alkaline, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous citric acid solution, water and an aqueous sodium chloride solution, in this order, dried and concentrated, and the obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5 to ethyl acetate) to obtain 5.3 g (yield: 77%) of N-[1-(4-formylpyrimidin-5-yl)-2-methylpropyl]-N-methyl-4-fluorophenylacetamide as colorless viscous liquid (nD20=1.5466).

Workup

  1. customreacted at room temperature for 5 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated
  4. additionan aqueous sodium hydrogencarbonate solution was added to alkaline
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with an aqueous citric acid solution, water
  7. dry with materialan aqueous sodium chloride solution, in this order, dried
  8. concentrationconcentrated
  9. customthe obtained oily product was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5 to ethyl acetate)

Sources & evidence

ORD record
ord-dc4d994f76cb4a70a69f7c6785f02148
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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