Sodium Carbonate → 2-Methyl-4-amino-5-pyrimidine aldoxime

HRID 414759Notes

Reaction equation

HRID 414759 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]=O)=[CH:4][N:3]=1.Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH:9]=[N:12][OH:13])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 129047264-Amino-2-methylpyrimidine-5-carbaldehyde

Product 1

HCID 855714892-Methyl-4-amino-5-pyrimidine aldoximeYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 8.6 g of 2-methyl-4-amino-5-formylpyrimidine and 340 ml of methanol, while stirring at room temperature, was added dropwise gradually 40 ml of an aqueous solution of 5.20 g of hydroxylamine hydrochloride and 7.80 g of sodium carbonate. As the reaction proceeded, crystals precipitated. Four hours later, the crystals were collected by filtration, washed with methanol and water, followed by drying under reduced pressure to give 7.84 g (82.3%) of 2-methyl-4-amino-5-pyrimidine aldoxime. The mother liquor was subjected to high performance liquid chromatography to quantitatively determine 2-methyl-4-amino-5-pyrimidine aldoxime (by absolute calibration curve method) to confirm that 1.41 g (14.8%) of the object compound was produced. The total yield of the crystals and the object compound in the mother liquor was 97.1%. The mother liquor was concentrated to dryness under reduced pressure, followed by recrystallization from a mixture solvent of methanol/ether to isolate 0.8 g of 2-methyl-4-amino-5-pyrimidine aldoxime.

Workup

  1. customcrystals precipitated
  2. filtrationFour hours later, the crystals were collected by filtration
  3. washwashed with methanol and water
  4. customby drying under reduced pressure

Sources & evidence

ORD record
ord-21b53de72e954b6d95ed91b21548e2c9
Source dataset
uspto-grants-1988_12
Patent number
US04794182

Reaction notes

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