Potassium Carbonate → HCID 178473140, compound

HRID 373225Notes

Reaction equation

HRID 373225 reaction equation
Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])[N:5]([CH2:46][CH3:47])[C:4](=[O:48])[CH:3]=1.[CH3:49][CH2:50][O:51][C:52]([CH2:54][SH:55])=[O:53].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:50]([O:51][C:52]([CH2:54][S:55][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])[N:5]([CH2:46][CH3:47])[C:4](=[O:48])[CH:3]=1)=[O:53])[CH3:49]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 19811545HCID 19811545, compound

Product 1

HCID 178473140HCID 178473140, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-3-ethyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.6 g), ethyl thioglycollate (0.13 ml) and potassium carbonate (0.19 g) in acetonitrile (10 ml) was heated under reflux for 10 hours with stirring. The reaction mixture was allowed to cool and the precipitate was removed by filtration. The filtrate was concentrated to dryness. The resulting residue was dissolved in methanol (15 ml) and 1N hydrochloric acid (1.5 ml), followed by stirring at room temperature for 7 hours. The reaction mixture was concentrated to dryness and then the residue was extracted with methylene chloride-water. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give pale yellow amorphous powders (0.15 g, 33%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureto cool
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  7. stirringby stirring at room temperature for 7 hours
  8. concentrationThe reaction mixture was concentrated to dryness
  9. extractionthe residue was extracted with methylene chloride-water
  10. washThe organic layer was washed with water
  11. customdried
  12. customevaporated to dryness
  13. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-122568c0e78a4b29aec48fe35a8c6837
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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