Acetamidine monohydrochloride → 5-(Dimethoxymethyl)-2-methylpyrimidin-4-amine

HRID 2412451Notes

Reaction equation

HRID 2412451 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].CO[CH:11]=[C:12]([CH:15]([O:18][CH3:19])[O:16][CH3:17])[C:13]#[N:14]>CO>[CH3:6][C:5]1[N:8]=[C:13]([NH2:14])[C:12]([CH:15]([O:18][CH3:19])[O:16][CH3:17])=[CH:11][N:7]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 538050392-(Dimethoxymethyl)-3-methoxyprop-2-enenitrile

Product 1

HCID 132362605-(Dimethoxymethyl)-2-methylpyrimidin-4-amineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a 50 ml four-necked flask equipped with a calciumchloride tube, a thermometer and a reflux condenser, there were placed 11.6 g (60 mmoles) of a 28 wt. % solution of sodium methylate in methanol and 10 ml of methanol. Thereto was added with stirring 5.67 g of acetamidine hydrochloride (60 mmoles) and the mixture was stirred at room temperature for 30 minutes. Then, 7.85 g (50 mmoles) of 2-methoxymethylene-3,3-dimethoxypropanenitrile was added thereto and the mixture was heated and refluxed for 5 hours. After completion of the reaction, the reaction mixture was cooled and then the insoluble sodium chloride was removed by filtration. After concentration of the solvent, methanol, 50 ml of water was added thereto and the mixture was extracted four times with 20 ml of methylene chloride. After the extract was dried over sodium sulfate, the sodium sulfate was removed by filtration and the filtrate was concentrated to dryness to obtain a white crude crystal. The thus obtained product was recrystallized from a mixed solvent of 50 ml of hexane and 25 ml of toluene to obtain 8.05 g (yield: 88%) of 2-methyl-4-amino-5-dimethoxymethylpyrimidine melting at 102°-104° C.

Workup

  1. customIn a 50 ml four-necked flask equipped with a calciumchloride tube
  2. additionThereto was added
  3. temperaturethe mixture was heated
  4. temperaturerefluxed for 5 hours
  5. customAfter completion of the reaction
  6. temperaturethe reaction mixture was cooled
  7. customthe insoluble sodium chloride was removed by filtration
  8. additionAfter concentration of the solvent, methanol, 50 ml of water was added
  9. extractionthe mixture was extracted four times with 20 ml of methylene chloride
  10. dry with materialAfter the extract was dried over sodium sulfate
  11. customthe sodium sulfate was removed by filtration
  12. concentrationthe filtrate was concentrated to dryness
  13. customto obtain a white crude crystal
  14. customThe thus obtained product was recrystallized from a mixed solvent of 50 ml of hexane and 25 ml of toluene

Sources & evidence

ORD record
ord-acedcb59b24d4e4d8a8704fa09d6835e
Source dataset
uspto-grants-1985_01
Patent number
US04492792

Reaction notes

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