Methylhydrazine → HCID 19917929, compound

HRID 1755872Notes

Reaction equation

HRID 1755872 reaction equation
CNN.[OH:4][C:5]1[C:6](=[O:25])[N:7]([CH3:24])[C:8]([CH2:11][O:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[N:9][CH:10]=1>CN(C)C=O>[NH2:13][O:12][CH2:11][C:8]1[N:7]([CH3:24])[C:6](=[O:25])[C:5]([OH:4])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 19918009HCID 19918009, compound

Product 1

HCID 19917929HCID 19917929, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylhydrazine (92 mg) (2 mmol) are added at 0° C. to a suspension of 301 mg (1 mmol) of N-[(3,4-dihydro-5-hydroxy-3-methyl-4-oxo-2-pyrimidinyl)methoxy]phthalimide in 9 ml of absolute dimethylformamide. A solution gradually results and this is then stirred at room temperature for 3 hours. The solution is concentrated in a high vacuum at room temperature, the residue is washed with petroleum ether and finally 10 ml of water are added thereto. After good intermixing the mixture is filtered. The filtrate is concentrated, finally with toluene/ethanol. After crystallization from ethanol there are obtained 125 mg of 2-[(aminooxy)methyl]-5-hydroxy-3-methyl-4(3H)-pyrimidinone as white crystals of m.p. 106° C.

Workup

  1. customA solution gradually results
  2. concentrationThe solution is concentrated in a high vacuum at room temperature
  3. washthe residue is washed with petroleum ether and finally 10 ml of water
  4. additionare added
  5. filtrationAfter good intermixing the mixture is filtered
  6. concentrationThe filtrate is concentrated, finally with toluene/ethanol
  7. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-77713f4599d64438b87fa4278811e8bf
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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