Ethanol → 2-Amino-6-methylpyrimidin-4-one

HRID 131056

Reaction equation

HRID 131056 reaction equation
C(O)C.C(=O)(O)O.[NH2:8][C:9]([NH2:11])=[NH:10].[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=O>O>[NH2:10][C:9]1[NH:11][C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[N:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8868Ethyl AcetoacetateHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 1354020552-Amino-6-methylpyrimidin-4-oneYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The above compound was prepared according to a literature method (Hirschberg, J. H. K., Beijer, F. H., van Aert, H. A., Magusin, P. C. M., Sijbesma, R. P., Meijer, E. W., Macromolecules, 1999, 32, 2696-2705, the disclosure of which is totally incorporated herein by reference). To a 1 liter round bottom flask under an inert argon atmosphere was added 650 milliliters of dry ethanol and 90.08 grams (0.5 mole) of guanidine carbonate. Thereafter, with good stirring was added dropwise over 2 hours 130.17 grams (1 mole) of ethyl acetoacetate, after which heat was applied and the mixture refluxed for 15 hours. The mixture was then cooled to room temperature and 800 milliliters of deionized water was slowly added to induce precipitation of the product. Subsequent vacuum filtration and washing with cold acetone secured the anticipated product in 68 percent yield (mp 311° C.). All physical properties were in accord with the reported properties.

Workup

  1. customThe above compound was prepared
  2. temperatureafter which heat
  3. temperaturethe mixture refluxed for 15 hours
  4. customprecipitation of the product
  5. filtrationSubsequent vacuum filtration
  6. washwashing with cold acetone

Sources & evidence

ORD record
ord-3ebf7000a2ef4496afad4a3828f42f67
Source dataset
uspto-grants-2008_06
Patent number
US07384463B2

Linked notes

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