Hydroxyamine hydrochloride → HCID 135482215, compound

HRID 1060863Notes

Reaction equation

HRID 1060863 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:21](=O)[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1[N:3]=[C:4](/[C:21](=[N:26]\[OH:27])/[CH2:22][CH3:23])[C:5]2[CH2:10][O:9][CH2:8][N:7]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 129702271-[7-methyl-1-(2,4,6-trimethyl-phenyl)-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-5-yl]-propan-1-one

Product 1

HCID 135482215HCID 135482215, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[7-methyl-1-(2,4,6-trimethyl-phenyl)-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-5-yl]-propan-1-one (50 mg, 0.154 mmol), hydroxylamine hydrochloride (43 mg, 0.62 mmol), and sodium acetate (57 mg, 0.693 mmol) in ethanol (4 ml) was stirred at room temperature overnight. The mixture was concentrated to dryness, then diluted with water, and extracted with 3 times with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness to give 51 mg of a mixture of the title (E) and (Z)-isomers as a white solid. Both isomers were separated by preparative thin layer chromatography plate with 40% ethyl acetate in hexane as solvent.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with water
  3. extractionextracted with 3 times with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ccda00da7bd84bda9e57431b1010e21d
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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