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

HRID 1742606
Notes
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Reaction equation

HRID 1742606 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.NO.C([O-])(=O)C.[Na+].CC(C1C(O)=CN=C(C=[N:38][OH:39])N=1)(C)C>C(O)C.O>[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:38][OH:39])[N:6]=1)([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehydeHCID 136378411(1,1-Dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde oxime

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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-his (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
  4. customgives the
  5. additionas a mixture of isomers (0.62 g, 39%)

Sources & evidence

ORD record
ord-a41abdf948d5410cac6fbc8407ce8360
Source dataset
uspto-grants-1994_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05340815

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes