Ethanol → HCID 18697995, compound

HRID 2289548Notes

Reaction equation

HRID 2289548 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.Cl.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:27])[CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(O)C>C(N(CC)CC)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([N:28]3[CH2:29][CH2:30][N:31]([C:6]4[N:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)[CH2:32][CH2:33]3)=[O:27])[CH2:22][CH2:21]2)(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 5817964-Chloro-6-methylpyrimidineHCID 18698038HCID 18698038, compound

Product 1

HCID 18697995HCID 18697995, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Methyl-6-chloropyrimidine (0.51 g) was added to a stirred mixture of 1-(4-bromophenylsulphonyl)-4-(1-piperazinylcarbonyl)piperazine hydrochloride (1.50 g) and ethanol (35 ml). Triethylamine (2.2 ml) was added and the mixture was heated at reflux for 6 hours. The solvent was removed by evaporation and the residue was purified by chromatography on silica gel using a gradient of 0% to 10% methanol in dichloromethane as eluent to give a foam. This was crystallised from methyl tert-butyl ether to give 1-(4-bromophenylsulphonyl)-4-[1-(4-methylpyrimidin-6-yl)piperazin-4-ylcarbonyl]piperazine as a solid (0.77 g); m.p. 215-216° C.; NMR (CDCl3): 8.5 (s, 1H), 7.7 (m, 2H), 7.6 (m, 2H), 6.35 (s, 1H), 3.6 (m, 4H), 3.4 (m, 4H), 3.3 (m, 4H), 3.05 (m, 4H), 2.33 (s, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed by evaporation
  4. customthe residue was purified by chromatography on silica gel using a gradient of 0% to 10% methanol in dichloromethane as eluent
  5. customto give a foam
  6. customThis was crystallised from methyl tert-butyl ether

Sources & evidence

ORD record
ord-58829d338d8344039fdf10939b57db81
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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