Thiophenol → 3-Butyl-6-phenylthio-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373224Notes

Reaction equation

HRID 373224 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8](Cl)[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4].[C:51]1([SH:57])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([S:57][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:27][N:28]=[N:29][N:30]=3)=[CH:18][CH:19]=2)[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 198115293-butyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1784486893-Butyl-6-phenylthio-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-butyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.52 g), thiophenol (0.1 ml) and potassium carbonate (0.15 g) in acetonitrile (10 ml) was heated under reflux for 4 hours with stirring. The reaction mixture was allowed to cool and the insoluble material was removed from the reaction mixture by filtration. The filtrate was concentrated to dryness. The resulting residue was dissolved in methanol (15 ml) and 1N hydrochloric acid (1 ml) and the mixture stirred at room temperature for 4 hours. The reaction mixture was concentrated to dryness and 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 colorless amorphous powders (0.27 g, 69%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. customthe insoluble material was removed from the reaction mixture by filtration
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  7. stirring1N hydrochloric acid (1 ml) and the mixture stirred at room temperature for 4 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-495cadec6e7d4e8cbd37cc8cef45c5a6
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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