Hydroxylamine, sulfate (1:1) → 2-Methyl-4-amino-5-pyrimidine aldoxime

HRID 414761Notes

Reaction equation

HRID 414761 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]=O)=[CH:4][N:3]=1.S(O)(O)(=O)=O.[NH2:16][OH:17]>CO.O>[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]=[N:16][OH:17])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 159255Hydroxylamine, sulfate (1:1)HCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Product 1

HCID 855714892-Methyl-4-amino-5-pyrimidine aldoximeYield 148.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 8.6 g of 2-methyl-4-amino-5-formylpyrimidine, while stirring at room temperature in a mixture of 340 ml of methanol and 40 ml of water, was added dropwise gradually 10 ml of an aqueous solution containing 6.10 g of hydroxylamine sulfate. As the reaction proceeded, crystals precipitated out. Four hours later, the crystals were collected by filtration, followed by drying under reduced pressure to give 10.5 g (83.5%) of 2-methyl-4-amino-5-pyrimidine aldoxime 1/2 sulfate. The mother liquor was subjected to quantitative deterimination (by absolute calibration curve method) of 2-methyl-4-amino-5-pyrimidine aldoxime 1/2 sulfate by means of high performance liquid chromatography to thereby confirm the production of 1.67 g (13.3%) of the object compound. The total yield of the crystals thus obtained and the object compound in the mother liquor was 96.8%. Physical properties of 2-methyl-4-amino-5-pyrimidine aldoxime 1/2 sulfate first obtained were as follows:

Workup

  1. customcrystals precipitated out
  2. filtrationFour hours later, the crystals were collected by filtration
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-89c033257f9140c286dcb20a7a576837
Source dataset
uspto-grants-1988_12
Patent number
US04794182

Reaction notes

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