Potassium Carbonate → 4'-{[3-(2-cyclohexyl-2-oxoethyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889374Notes

Reaction equation

HRID 1889374 reaction equation
[CH2:1]([C:3]1[S:28][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[CH:29]1([CH:35]2[CH2:37][O:36]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.O.C(OCC)(=O)C.CN(C)C=O>[CH:29]1([C:35](=[O:36])[CH2:37][N:9]2[C:10](=[O:11])[C:5]3[CH:4]=[C:3]([CH2:1][CH3:2])[S:28][C:6]=3[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)[C:8]2=[O:12])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 82029Methyl morpholine oxideHCID 942642-CyclohexyloxiraneHCID 593517704'-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 593516544'-{[3-(2-cyclohexyl-2-oxoethyl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileYield 52%

Reagents, catalysts & solvents 5

HCID 178419074HCID 178419074, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4′-[(6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (1 g), 2-cyclohexyloxirane (0.98 g), potassium carbonate (0.71 g) and N,N-dimethylformamide (13 mL) was stirred at 80° C. for 20 hr. After allowing to cool to room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by silica gel column chromatography was dissolved in methylene chloride (8 mL), 4-methylmorpholine-N-oxide (0.34 g), tetrapropylammonium perruthenate (0.026 g) and molecular sieves 4A (0.15 g) were added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and silica gel column chromatography gave the title compound as a colorless solid (0.68 g, 52%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue obtained by silica gel column chromatography
  7. stirringthe mixture was stirred at room temperature for 3 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure, and silica gel column chromatography

Sources & evidence

ORD record
ord-1974a0d256be4dd9a4cbf758204a6a11
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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