Potassium Carbonate → HCID 136026746, compound

HRID 1673604Notes

Reaction equation

HRID 1673604 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[NH:5][C:4](=[O:11])[C:3]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]=[C:36](C(Cl)(Cl)Cl)[O:35][N:34]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-:43].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][C:36](=[O:43])[O:35][N:34]=3)=[CH:23][CH:22]=2)[C:4](=[O:11])[C:3]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15290996HCID 15290996, compoundHCID 136026747HCID 136026747, compound

Product 1

HCID 136026746HCID 136026746, compoundYield 4.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-methyl-2-propyl-5-(pyridin-2-ylmethyl)pyrimidin-4(3H)-one (0.51 g) and 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (1.0 g) in acetonitrile (20 mL) was added potassium carbonate (0.58 g), and the mixture was stirred for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran-ethanol (1:1, 4 mL), 1 M sodium hydroxide (2 mL) was added and the mixture was stirred for 30 min. The reaction mixture was weakly acidified with 1 M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.043 g, 4%) as a pale-yellow solid.

Workup

  1. washwashed with 1 M hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran-ethanol (1:1, 4 mL)
  5. addition1 M sodium hydroxide (2 mL) was added
  6. stirringthe mixture was stirred for 30 min
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4023fd4db7e940feb8d0781107e2dc85
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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