Acetic Anhydride → 6-Amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione

HRID 224583Notes

Reaction equation

HRID 224583 reaction equation
[C:1](CC(O)=O)#[N:2].C(O[C:11](=[O:13])[CH3:12])(=O)C.[CH3:14][NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17]>C(O)(=O)C>[NH2:2][C:1]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:17])[N:15]([CH3:14])[C:11](=[O:13])[CH:12]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 138801-Methyl-3-phenylurea

Product 1

HCID 16492566-Amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 38 g (0.44 mol) of cyanacetic acid, 200 ml of acetic anhydride and 200 ml of acetic acid was added 60 g of 1-methyl-3-phenylurea. The solution was stirred at 90°-100° C. for some hours. After cooling, 65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C). This was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution was added. After cooling and filtration, the filtrate was evaporated and the crystals were washed with ethanol. Yield 46.7 g (XVI) NMR.

Workup

  1. temperatureAfter cooling
  2. filtration65.5 g of 1-cyanoaceto-1-methyl-3-phenylurea (XV) was filtered off (mp 180° C)
  3. dissolutionThis was dissolved in 3 1 of boiling ethanol and 10 ml of 10% soda solution
  4. additionwas added
  5. temperatureAfter cooling
  6. filtrationfiltration
  7. customthe filtrate was evaporated
  8. washthe crystals were washed with ethanol

Sources & evidence

ORD record
ord-5cf4bfa389b841779054e5b8b4274489
Source dataset
uspto-grants-1980_11
Patent number
US04233303

Reaction notes

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