Potassium Carbonate → 2-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-benzyloxypyrimidine

HRID 1757061Notes

Reaction equation

HRID 1757061 reaction equation
[Br-].[CH2:2]([O:9][C:10]1[CH:11]=[N:12][C:13]([N:16]2[CH2:25][CH2:24][N+:19]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:26][C:27]1[N:28]=[C:29]([CH3:33])[NH:30][C:31]=1[Cl:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:26][C:27]1[N:28]=[C:29]([CH3:33])[N:30]([CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[CH2:18][CH2:17][N:16]([C:13]3[N:12]=[CH:11][C:10]([O:9][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:15][N:14]=3)[CH2:25][CH2:24]2)[C:31]=1[Cl:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3123904,5-Dichloro-2-methyl-1H-imidazoleHCID 193897838-(5-Benzyloxy-2-pyrimidinyl)-8-aza-5-azoniaspiro [4.5]decane bromide

Product 1

HCID 193897772-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-benzyloxypyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.59 g (8.85 mmol) of 8-(5-benzyloxy-2-pyrimidinyl)-8-aza-5-azoniaspiro [4.5]decane bromide, 1.47 g (9.73 mmol) of 4,5-dichloro-2-methylimidazole and 4.89 g (35.41mmol) of potassium carbonate in 72 ml of dimethylformamide is refluxed for 12 hours and filtered hot. The dimethylformamide is evaporated and the product is chromatographed on silica gel, yielding 2.90 g (69%) of 2-{4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-1-piperazinyl}-5-benzyloxypyrimidine.

Workup

  1. temperatureis refluxed for 12 hours
  2. filtrationfiltered hot
  3. customThe dimethylformamide is evaporated
  4. customthe product is chromatographed on silica gel

Sources & evidence

ORD record
ord-23519f1e3d80464490782dbae46a853e
Source dataset
uspto-grants-1995_08
Patent number
US05444059

Reaction notes

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