Ammonium Chloride → HCID 57460836, compound

HRID 1718867Notes

Reaction equation

HRID 1718867 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15](=[O:16])[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]=[C:11]2[CH2:35][CH3:36])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:37][Li].[Cl-].[NH4+]>O1CCCC1>[CH2:35]([C:11]1[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([OH:3])([CH3:37])[CH3:2])[CH:5]=2)[C:15](=[O:16])[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)=[C:13]([CH2:32][CH2:33][CH3:34])[N:12]=1)[CH3:36]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57460835HCID 57460835, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57460836HCID 57460836, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4′-{[1-(3-acetylphenyl)-2-ethyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (0.63 g) in tetrahydrofuran (10 mL) was added methyllithium (1.2 mL, 2.2 M diethyl ether solution) under ice-cooling, and the mixture was stirred for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, 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 as a pale-yellow solid (0.54 g, 83%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-748fcc2acb9c48f48785199218b431f1
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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