Methanethiol → 6-Methylthio-3-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373215Notes

Reaction equation

HRID 373215 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][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1.[CH3:50][SH:51].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:50][S:51][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][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1784565476-Methylthio-3-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.6 g), methylmercaptan (15%, 0.51 g) and potassium carbonate (0.13 g) in acetonitrile (10 ml) was heated under reflux for 6 hours with stirring. The insoluble material was removed from the reaction mixture by filtration and the filtrate was concentrated to dryness. The resulting residue was dissolved in methanol (15 ml) and then 1N hydrochloric acid (1 ml) was added to the solution, followed by stirring at room temperature for 3 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 colorless powders (0.22 g, 54%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe insoluble material was removed from the reaction mixture by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  6. addition1N hydrochloric acid (1 ml) was added to the solution
  7. stirringby stirring at room temperature for 3 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-6965d06b757b4c11971855a29568686f
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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