Acetonitrile → HCID 12151353, compound

HRID 393148Notes

Reaction equation

HRID 393148 reaction equation
[CH2:1]([O:3][CH:4]([O:17][CH2:18][CH3:19])[C:5]1[C:10]([CH:11]([NH:15][CH3:16])[CH:12]([CH3:14])[CH3:13])=[CH:9][N:8]=[CH:7][N:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(#N)C.[C:29]1([CH2:35][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:1]([O:3][CH:4]([O:17][CH2:18][CH3:19])[C:5]1[C:10]([CH:11]([N:15]([CH3:16])[C:36](=[O:37])[CH2:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:12]([CH3:13])[CH3:14])=[CH:9][N:8]=[CH:7][N:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7679Phenylacetyl chlorideHCID 11430Potassium CarbonateHCID 12151356HCID 12151356, compound

Product 1

HCID 12151353HCID 12151353, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.3 g (0.031 mol) of [1-(4-diethoxymethylpyrimidin-5-yl)-2-methylpropyl]methylamine and 6.4 g (46 mmol) of potassium carbonate were added to 100 ml of acetonitrile, and then 5.8 g (0.038 mol) of phenylacetyl chloride was dropwise added at room temperature and reacted for 2 hours. After completion of the reaction, the product was poured into water and extracted 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 8.4 g (yield: 70%) of N-[1-(4-diethoxymethylpyrimidin-5-yl)-2-methylpropyl]-N-methyl-2-phenyl acetamide as colorless viscous liquid (nD2=1.5253)

Workup

  1. customreacted for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous citric acid solution, water
  5. dry with materialan aqueous sodium chloride solution in this order, dried
  6. concentrationconcentrated
  7. 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-c671939eaf8c42acaa2cb19b5fa7318f
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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