Ethyl 2-methylacetoacetate → 5,6-dimethyl-2-(4-methylphenyl)-3H-pyrimidin-4-one

HRID 22252

Reaction equation

HRID 22252 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[NH:7])=[CH:4][CH:3]=1.[CH3:11][CH:12]([C:18]([CH3:20])=O)[C:13](OCC)=[O:14]>C(O)C>[CH3:11][C:12]1[C:13](=[O:14])[NH:7][C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)=[N:8][C:18]=1[CH3:20]

Participants

4

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 1227544-Toluamidine

Product 1

HCID 1357047395,6-dimethyl-2-(4-methylphenyl)-3H-pyrimidin-4-oneYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methylbenzamidine (4.4 g) in 30 ml of ethanol was added ethyl 2-methylacetoacetate (6.1 g), and the mixture refluxed for 4 hours, giving a precipitate. The mixture was cooled to 0° C., the solid filtered off, washed with ethanol, and dried under reduced pressure, yielding 6 g of 5,6-dimethyl-2-(4-methylphenyl)-3H-pyrimidin-4-one, m.p. 250° C.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. customgiving a precipitate
  3. filtrationthe solid filtered off
  4. washwashed with ethanol
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-858249ef680649c6831afda0b40f7b35
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Linked notes

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