Water → Ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate

HRID 979140Notes

Reaction equation

HRID 979140 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]([NH2:15])=[NH:14])[CH2:2][CH2:3][CH3:4].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C.O>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[NH:15][C:19](=[O:18])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 178450125HCID 178450125, compound

Product 1

HCID 13562779Ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylateYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(2-butoxyphenyl)guanidine (11.6 g) and diethyl ethoxymethylenemalonate (12.1 g) in DMF (70 ml) is heated at 100° C. for 9 hours. After cooling, water (50 ml) is added to the reaction mixture, and the precipitate is collected by filtration, washed with ethanol and recrystallized from a mixture of DMF and water to give ethyl 2-(2-butoxyanilino)-1,6-dihydro-6-oxo-5-pyrimidinecarboxylate (16.1 g). M.p. 211°-213° C.

Workup

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

Sources & evidence

ORD record
ord-d3722d8ab3ac48aca6d34b471d0c0492
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Reaction notes

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