Diethyl (ethoxymethylene)malonate → Ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylate

HRID 979139Notes

Reaction equation

HRID 979139 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([NH2:14])=[NH:13])[CH2:2][CH3:3].C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>O1CCOCC1>[O:17]=[C:18]1[NH:14][C:12]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:1][CH2:2][CH3:3])=[N:13][CH:25]=[C:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178458330HCID 178458330, compound

Product 1

HCID 13562777Ethyl 1,6-dihydro-2-(2-propoxyanilino)-6-oxo-5-pyrimidinecarboxylateYield 78.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(2-propoxyphenyl)guanidine (9.1 g) in dioxane (30 ml) is added dropwise diethyl ethoxymethylenemalonate (10.2 g), and the mixture is refluxed with stirring for 5 hours. After cooling, the precipitate is collected by filtration and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-6-oxo-2-(2-propoxyanilino)-5-pyrimidinecarboxylate (11.7 g). M.p. 198°-200° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe precipitate is collected by filtration
  4. customrecrystallized from a mixture of DMF and water

Sources & evidence

ORD record
ord-5920b58a0e2f4c0995a71d2ed3b8e6eb
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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