Trifluoroacetic acid → 4,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

HRID 1742605Notes

Reaction equation

HRID 1742605 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]([C:12]1[C:17]([O:18]COCCOC)=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[N:15]=[C:14]([CH:29]=[O:30])[N:13]=1)([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][C:9]([C:12]1[C:17]([OH:18])=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[N:15]=[C:14]([CH:29]=[O:30])[N:13]=1)([CH3:8])[CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 199229924,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde

Product 1

HCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehydeYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.05 g, 9.2 retool) is added to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2 -methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde (1.0 g, 3.1 mmol) in methylene chloride and the reaction mixture is stirred at room temperature for 5 hours. The reaction mixture is neutralized by the addition of saturated aqueous NaHCO3 and the layers separated. The organic layer is washed with brine (50 mL), dried over MgSO4, and evaporated. Recrystallization of the residue from hexane gives pure 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (0.24 g, 33%); mp 187°-189° C.

Workup

  1. customthe layers separated
  2. washThe organic layer is washed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customRecrystallization of the residue from hexane

Sources & evidence

ORD record
ord-3b6b6a784b3a4188b9dd1b30f3d2b0e2
Source dataset
uspto-grants-1994_08
Patent number
US05340815

Reaction notes

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