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

HRID 2412452Notes

Reaction equation

HRID 2412452 reaction equation
C[O-].[Na+].Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].[CH3:9][O:10][CH:11]([O:20][CH3:21])[CH:12]([CH:15](OC)OC)[C:13]#[N:14]>CO>[CH3:6][C:5]1[N:8]=[C:13]([NH2:14])[C:12]([CH:11]([O:20][CH3:21])[O:10][CH3:9])=[CH:15][N:7]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 133658082-(Dimethoxymethyl)-3,3-dimethoxypropanenitrile

Product 1

HCID 132362605-(Dimethoxymethyl)-2-methylpyrimidin-4-amineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same reaction apparatus as in Example 9, there was placed 11.6 g (60 mmoles) of a 28 wt. % solution of sodium methylate in methanol. Thereto was added with stirring 5.67 g (60 mmoles) of acetamidine hydrochloride, and the mixture was stirred at room temperature for one hour. Subsequently, 9.45 g (50 mmoles) of 2-dimethoxymethyl-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 the insoluble sodium chloride was removed by filtration. The filtrate was analyzed by gas chromatography according to the internal standard method. As the result, it was confirmed that 8.51 g (yield: 93%) of 2-methyl-4-amino-5-dimethoxymethylpyrimidine had been formed.

Workup

  1. additionThereto was added
  2. temperaturethe mixture was heated
  3. temperaturerefluxed for 5 hours
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled
  6. customthe insoluble sodium chloride was removed by filtration

Sources & evidence

ORD record
ord-55ffb0a20d4d458c871a2add8bca4682
Source dataset
uspto-grants-1985_01
Patent number
US04492792

Reaction notes

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