Diethyl (ethoxymethylene)malonate → Ethyl 1,6-dihydro-2-[2-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate

HRID 979142Notes

Reaction equation

HRID 979142 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([NH2:14])=[NH:13].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>>[CH3:1][CH:2]([CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]1[NH:14][C:19](=[O:18])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][N:13]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 178450124HCID 178450124, compound

Product 1

HCID 13562780Ethyl 1,6-dihydro-2-[2-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylateYield 66.1%

Procedure

To a solution of N-[2-(2-methylpropoxy)phenyl]guanidine (89 g) in denatured alcohol (300 ml) is added dropwise diethyl ethoxymethylenemalonate (93 g), and the mixture is refluxed with stirring for 3 hours. After cooling, the precipitate is collected by filtration, washed with denatured alcohol and petroleum ether and dried to give ethyl 1,6-dihydro-2-[2-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (94 g). M.p. 188°-190° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe precipitate is collected by filtration
  4. washwashed with denatured alcohol and petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-c137b016863747588082916e50935601
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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