Potassium Carbonate → 2-(4-Benzylpiperazin-1-yl)-4,6-dimethoxypyrimidine

HRID 440240Notes

Reaction equation

HRID 440240 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1>C(#N)C>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([N:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)[N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 46128712-(4-Benzylpiperazin-1-yl)-4,6-dimethoxypyrimidineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 100 ml of acetonitrile was dissolved 10 g (0.0567 mole) of 1-benzylpiperazine, and 11.7 g (0.085 mole) of potassium carbonate and 14.8 g (0.068 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added thereto. The mixture was refluxed by heating for 5 hours. The mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of ethyl acetate : toluene = 1 : 9) to obtain 17.6 g of 4-(4,6-dimethoxy-2-pyrimidinyl)-1-benzylpiperazine as colorless liquid.

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 5 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additiona mixture of ethyl acetate

Sources & evidence

ORD record
ord-7954dd196cdc4d4a817bf70dc9e306fa
Source dataset
uspto-grants-1996_05
Patent number
US05519016

Reaction notes

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