Potassium Carbonate → N-(4-((4-(4,6-dimethoxypyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282155Notes

Reaction equation

HRID 1282155 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:20]1[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:29][O:28][C:22]1[CH:23]=[C:24]([O:26][CH3:27])[N:25]=[C:20]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][C:8]3[CH:9]=[CH:10][C:11]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=3)[CH2:2][CH2:3]2)[N:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51523232-Chloro-4,6-dimethoxypyrimidineHCID 18423078N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 11574555N-(4-((4-(4,6-dimethoxypyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamideYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide (5.0 g) obtained in Example 88(2), 2-chloro-4,6-dimethoxypyrimidine (3.9 g) and potassium carbonate (4.2 g) in acetonitrile (50 ml) was refluxed under heating for 5 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-brown solid. The obtained pale-brown solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) and crystallized from diisopropyl ether to give the title compound (5.0 g) as white crystals.

Workup

  1. temperatureunder heating for 5 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a pale-brown solid
  7. customThe obtained pale-brown solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1)
  8. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-13c4a20437a246a4adce3bc9e467a0e9
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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