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

HRID 1699436Notes

Reaction equation

HRID 1699436 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:17][CH2:16][N+:11]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[Cl:18][C:19]1[N:20]=[C:21]([CH3:25])[NH:22][C:23]=1[Cl:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:18][C:19]1[N:20]=[C:21]([CH3:25])[N:22]([CH2:12][CH2:13][CH2:14][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)[CH2:17][CH2:16]2)[C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3123904,5-Dichloro-2-methyl-1H-imidazoleHCID 120447898-(5-Fluoro-2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane

Product 1

HCID 98083422-(4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.17 g (0.01 mol) of 8-(5-fluoro-2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane, 2.26 g (0.015 mol) of 4,5-dichloro-2-methyl-1H-imidazole and 76 g (0.02 mol) of potassium carbonate in 80 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. 3.3 g (85% 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-27078bcc6fc3413fa4bc9d9150cb1a8b
Source dataset
uspto-grants-2002_02
Patent number
US06346620B1

Reaction notes

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