Hydroxylamine, N-chloro- → [-2,5,6-Trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propan-1-one oxime

HRID 1884352

Reaction equation

HRID 1884352 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:22](=O)[CH2:23][CH3:24])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:6]=2[N:7]=1.[OH:26][NH:27]Cl.C([O-])(=O)C.[Na+]>CO>[CH3:1][C:2]1[N:3]=[C:4]([C:22](=[N:27][OH:26])[CH2:23][CH3:24])[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 149953Hydroxylamine, N-chloro-HCID 517045Sodium AcetateHCID 235057331-[-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propan-1-one

Product 1

HCID 136388382[-2,5,6-Trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propan-1-one oximeYield 105.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propan-1-one (0.598 g, 1.783 mmol), hydroxylamino hydrochloride (0.370 g, 5.35 mmol), sodium acetate (0.439 g, 5.35 mmol) in MeOH (30 ml) was stirred at room temperature for 24 hours. The mixture was concentrated to dryness. The residue was diluted with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 0.657 g of a white glassy foam. The glassy foam was purified through silica gel column chromatography to separated both E (white crystals, mp 162-164° C., confirmed by X-ray structural analysis) and Z (white crystals, mp 84-87° C.) isomers and a mixture of E and Z isomers (mp −150-190° C.).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-225afdbf07f94301875f13f8b1633af3
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Linked notes

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