Propyl mercaptan → 3-Butyl-6-propylthio-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373243Notes

Reaction equation

HRID 373243 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:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4].[CH2:51]([SH:54])[CH2:52][CH3:53].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([S:54][CH2:51][CH2:52][CH3:53])[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:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:6]1=[O:50])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 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 198115243-Butyl-6-propylthio-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 68%

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 (1.4 g), propylmercaptan (0.24 ml) and potassium carbonate (0.35 g) in acetonitrile (25 ml) was heated under reflux for 3 hours. The reaction mixture was allowed to cool and the precipitate was removed by filtration. The filtrate was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel to give colorless amorphous powders (1 g, 68%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated to dryness
  6. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-64d9b91b276448b792406ed2a94d7722
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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