Water → 4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde oxime

HRID 1647418Notes

Reaction equation

HRID 1647418 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=O)[N:6]=1)([CH3:4])[CH3:3].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=[N:19][OH:20])[N:6]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

Product 1

HCID 1363784134,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.5 g, 6.3 mmol), hydroxylamine hydrochloride (2.2 g, 32.7 mmol), and sodium acetate (2.9 g, 34.9 mmol) in ethanol (20 mL) is heated at reflux for 12 hours. The reaction mixture is poured over water (150 mL) and the precipitate is collected by filtration. Recrystallization from ether/hexane gives the desired 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde oxime as a mixture of isomers (0.62 g, 39%); mp 205°-220° C.

Workup

  1. temperatureat reflux for 12 hours
  2. filtrationthe precipitate is collected by filtration
  3. customRecrystallization from ether/hexane

Sources & evidence

ORD record
ord-e1b8e9408d9d402e8be66ebae1238091
Source dataset
uspto-grants-1995_07
Patent number
US05432181

Reaction notes

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