Trityl chloride → 5-Phenyl-2-(trityl-amino)-pyridin-3-ol

HRID 425884Notes

Reaction equation

HRID 425884 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1.[H-].[Na+].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[C:9]1([C:5]2[CH:6]=[C:7]([OH:8])[C:2]([NH:1][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 211113862-Amino-5-phenylpyridin-3-ol

Product 1

HCID 211114995-Phenyl-2-(trityl-amino)-pyridin-3-olYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-phenyl-pyridin-3-ol (2.04 g, 10.95 mmol) in THF (anhydrous, 30 mL) was added NaH (1.31 g, 32.85 mmol) slowly. The mixture was stirred under nitrogen for 20 minutes, and then trityl chloride (3.66 g, 13.14 mmol) was added. The reaction was stirred at room temperature for over night under nitrogen. The solvent was evaporated, and the residue was dissolved in dichloromethane, washed with water, and dried over Na2SO4. After filtration and condensation, the crude product was purified on a silica gel column eluting with EtOAc-Hexane (1:10) to provide 5-phenyl-2-(trityl-amino)-pyridin-3-ol (1.09 g, 23% yield). MS m/z 427 [M+1].

Workup

  1. stirringThe reaction was stirred at room temperature for over night under nitrogen
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and condensation
  7. customthe crude product was purified on a silica gel column
  8. washeluting with EtOAc-Hexane (1:10)

Sources & evidence

ORD record
ord-75823886d2224e1d93e410c9f5908afe
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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