4-Chloropyrimidine → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(4-pyrimidinylthio)butyramide

HRID 52122

Reaction equation

HRID 52122 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][S:24][C:25](=O)[CH3:26])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].Cl[C:33]1C=C[N:36]=[CH:35][N:34]=1>CO>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][S:24][C:25]3[CH:26]=[CH:33][N:34]=[CH:35][N:36]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6428344-ChloropyrimidineHCID 10942334Sodium MethoxideHCID 86750623N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(acetylthio)butyramide

Product 1

HCID 67725816N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(4-pyrimidinylthio)butyramideYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1.00 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-4-(acetylthio)butyramide [prepared as described in step (a) above] in 10 ml of methanol was added to a mixture of 0.48 g of 28% w/v methanolic sodium methoxide and 5 ml of methanol, whilst ice-cooling, and the mixture was stirred at the same temperature for 20 minutes. At the end of this time, 0.28 g of 4-chloropyrimidine was added to the mixture and the mixture was heated under reflux for 2 hours. The solvent was then removed by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The solvent was removed from the extract by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.65 g (yield 60%) of the title compound as an oil.

Workup

  1. temperaturewhilst ice-cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThe solvent was then removed by evaporation under reduced pressure, and water
  5. additionwas added to the resulting residue, which
  6. extractionwas then extracted with ethyl acetate
  7. customThe solvent was removed from the
  8. extractionextract by distillation under reduced pressure
  9. customthe residue was purified by column chromatography through silica gel
  10. additionby volume mixture of ethanol and chloroform as the eluent

Sources & evidence

ORD record
ord-5fa4ab07a0464c2bb448710a3a085937
Source dataset
uspto-grants-1997_04
Patent number
US05616579

Linked notes

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