Propyl mercaptan → 1-(2'-cyanobiphenyl-4-yl)methyl-3-propyl-6-propylthiopyrimidine-2,4(1H,3H)-dione

HRID 373244Notes

Reaction equation

HRID 373244 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]#[N:22])=[CH:11][CH:10]=2)[C:6](=[O:23])[N:5]([CH2:24][CH2:25][CH3:26])[C:4](=[O:27])[CH:3]=1.[CH2:28]([SH:31])[CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:7]2[C:2]([S:31][CH2:28][CH2:29][CH3:30])=[CH:3][C:4](=[O:27])[N:5]([CH2:24][CH2:25][CH3:26])[C:6]2=[O:23])=[CH:10][CH:11]=1)#[N:22]

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 198115376-chloro-1-(2'-cyanobiphenyl-4-yl)methyl-3-propylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 198115231-(2'-cyanobiphenyl-4-yl)methyl-3-propyl-6-propylthiopyrimidine-2,4(1H,3H)-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-1-(2'-cyanobiphenyl-4-yl)methyl-3-propylpyrimidine-2,4(1H,3H)-dione (0.7 g), propylmercaptan (0.2 ml) and potassium carbonate (0.51 g) in acetonitrile (12 ml) was stirred 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 to give colorless syrups (0.77 g, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. extractionthe residue was extracted with methylene chloride-water
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-6e5ecd3a70ac4ebe8de44462170aec63
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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