Potassium Carbonate → 2-(4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine

HRID 380328Notes

Reaction equation

HRID 380328 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl[CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[C:23]([Cl:24])=[C:22]([Cl:25])[N:21]=[C:20]1[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:25][C:22]1[N:21]=[C:20]([CH3:26])[N:19]([CH2:18][CH2:17][CH2:16][CH2:15][N:11]2[CH2:10][CH2:9][N:8]([C:5]3[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=3)[CH2:13][CH2:12]2)[C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100581585-Fluoro-2-(piperazin-1-yl)pyrimidineHCID 183205531-(4-chlorobutyl)-4,5-dichloro-2-methyl-1H-imidazole

Product 1

HCID 98083422-(4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.5 g (0.02 mol) of 5-fluoro-2-(piperazin-1-yl)pyrimidine, 6.04 g (0.025 mol) of 1-(4-chlorobutyl)-4,5-dichloro-2-methyl-1H-imidazole and 4.14 g (0.03 mol) of potassium carbonate in 200 ml of dimethylformamide is maintained at reflux for 12 hours. The mixture is subsequently evaporated to dryness and the resulting crude product is redissolved in chloroform and washed repeatedly with water. The organic phase is dried and evaporated, and then the resulting crude product is purified by chromatography on a column of silica gel. 6.4 g (83% yield) of 2-{4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-piperazin-1-yl}-5-fluoropyrimidine are obtained in the form of an oil.

Workup

  1. temperatureis maintained
  2. temperatureat reflux for 12 hours
  3. customThe mixture is subsequently evaporated to dryness
  4. dissolutionthe resulting crude product is redissolved in chloroform
  5. washwashed repeatedly with water
  6. customThe organic phase is dried
  7. customevaporated
  8. customthe resulting crude product is purified by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-ba0b321007b146d79f6d61974af15c30
Source dataset
uspto-grants-2001_10
Patent number
US06303608B1

Reaction notes

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