tert-Butyl mercaptan → HCID 178454938, compound

HRID 373226Notes

Reaction equation

HRID 373226 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11](Cl)[N:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:9]1=[O:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:54]([SH:58])([CH3:57])([CH3:56])[CH3:55].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([S:58][C:54]([CH3:57])([CH3:56])[CH3:55])[N:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[NH:33][N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:9]1=[O:53])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 198115483-benzyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 178454938HCID 178454938, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-benzyl-6-chloro-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.5 g), tert-butylmercaptan (0.1 ml) and potassium carbonate (0.14 g) in acetonitrile (10 ml) was heated under reflux for 8 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 ml) and the mixture was stirred at room temperature for 4 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 (0.2 g, 54%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 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. stirring1N hydrochloric acid (1 ml) and the mixture was 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-94cddd58c3994aea8533f2a428d56d77
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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