Water → N-(2-Chloro-4-methylpyrimidin-5-yl)acetamide

HRID 34089Notes

Reaction equation

HRID 34089 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].O>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH:9][C:16](=[O:18])[CH3:17])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 3162822-Chloro-4-methylpyrimidin-5-amine

Product 1

HCID 23070222N-(2-Chloro-4-methylpyrimidin-5-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.36 g of 2-chloro-4-methylpyrimidin-5-ylamine was dissolved in 20 mL of dichloromethane, and under stirring on ice, 1.53 mL of pyridine, 2.7 mL of acetic anhydride and 1.16 g of 4-dimethylaminopyridine were added. After stirring at room temperature for 1 hour, water was added, extracted with ethyl acetate, and the resultant organic layer was washed with saturated brine and dried over magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1), to afford 178 mg of the title compound as a brown oil.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washthe resultant organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-a9d8a04fa4bf475faa7f0fe22aa09162
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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