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

HRID 373216Notes

Reaction equation

HRID 373216 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.[CH2:50]([SH:52])[CH3:51].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:50]([S:52][C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:22][N:23]=[N:24][N:25]=3)=[CH:13][CH:14]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1)[CH3:51]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 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 1784565466-Ethylthio-3-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

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), ethylmercaptan (0.08 ml) and potassium carbonate (0.25 g) in acetonitrile (10 ml) was heated at 70° C. for 2 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 (2 ml) was added to the solution, followed by stirring at room temperature for 21 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 (0.2 g, 48%).

Workup

  1. customThe insoluble material was removed from the reaction mixture by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  4. addition1N hydrochloric acid (2 ml) was added to the solution
  5. stirringby stirring at room temperature for 21 hours
  6. concentrationThe reaction mixture was concentrated to dryness
  7. extractionthe residue was extracted with methylene chloride-water
  8. washThe organic layer was washed with water
  9. customdried
  10. customevaporated to dryness
  11. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bca61d2564484236aa0f5a5b9a08de1d
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

Loading…