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

HRID 1707980
Notes
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Reaction equation

HRID 1707980 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 702
Ethanol
Solvent

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-e48af49ec49f4a18845314118cb43b41
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05356898

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes