Butyl iodide → HCID 136146815, compound

HRID 1674143Notes

Reaction equation

HRID 1674143 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH3:27])[NH:8][C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].I[CH2:31][CH2:32][CH2:33][CH3:34].[Cl-].O[NH3+:37].[C:38](=[O:41])([O-])[OH:39].[Na+]>C(OCC)(=O)C.CS(C)=O.CN(C)C=O>[CH2:31]([N:8]1[C:9](=[O:26])[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:37][C:38](=[O:41])[O:39][N:25]=3)=[CH:14][CH:13]=2)=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:6]=[C:7]1[CH3:27])[CH2:32][CH2:33][CH3:34]

Participants

9

Reactant 5

HCID 10962Butyl iodideHCID 21645Hydroxylamine HClHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 1354012224'-[(4-Butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 136146815HCID 136146815, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4′-[(4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1 g), sodium hydride (0.17 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 10 min, 1-iodobutane (0.64 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogen sulfate solution and then with 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 dimethyl sulfoxide (5 mL) and added to a mixture of hydroxylammonium chloride (1.27 g), sodium hydrogen carbonate (2.05 g) and dimethyl sulfoxide (10 mL), which had been mixed at 40° C. for 30 min. The reaction mixture was stirred at 90° C. for 16 hr, diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in tetrahydrofuran (20 mL). N,N′-carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.20 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogen sulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.24 g, 42%).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. washwashed with 5% aqueous potassium hydrogen sulfate solution
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue obtained by silica gel column chromatography
  6. additionhad been mixed at 40° C. for 30 min
  7. stirringThe reaction mixture was stirred at 90° C. for 16 hr
  8. washwashed with water
  9. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. dissolutionthe residue was dissolved in tetrahydrofuran (20 mL)
  12. additionN,N′-carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.20 mL) were added
  13. stirringthe mixture was stirred at room temperature for 2 hr
  14. additionThe reaction mixture was diluted with ethyl acetate
  15. washwashed with saturated aqueous potassium hydrogen sulfate solution
  16. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  17. customThe solvent was evaporated under reduced pressure
  18. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7bd7eb944ca4d5c87b5ded46c7a4a81
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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