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

HRID 414760Notes

Reaction equation

HRID 414760 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.O>[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

6

Reactant 3

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

Product 1

HCID 855714892-Methyl-4-amino-5-pyrimidine aldoximeYield 78.2%

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 272 ml of methanol and 68 ml of water, was added dropwise 10 ml of an aqueous solution containing 5.1 g of hydroxylamine hydrochloride. The reaction was allowed to proceed for further 4 hours at room temperature. To the reaction solution was added dropwise 30 ml of an aqueous solution containing 3.90 g of sodium carbonate to cause precipitation of crystals. The crystals were collected by filtration and dried under reduced pressure to give 7.45 g (yield 78.2%) of 2-methyl-4-amino-5-pyrimidine aldoxime. The mother liquor was subjected to quantitative determination (by absolute calibration curve method) of 2-methyl-4-amino-5-pyrimidine aldoxime by means of high performance liquid chromatography to confirm that 1.95 g (yield 20.5%) of the object compound was produced. The total yield of the crystals thus obtained and the object compound in the mother liquor was 98.7%.

Workup

  1. customprecipitation of crystals
  2. filtrationThe crystals were collected by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-844ec877e085414c9c3e03221eb67c56
Source dataset
uspto-grants-1988_12
Patent number
US04794182

Reaction notes

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