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

HRID 979111

Reaction equation

HRID 979111 reaction equation
CS[C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1.[CH2:15]([O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22])[CH2:16][CH2:17][CH3:18]>N1C=CC=CC=1>[CH2:15]([O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1)[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 1382652-ButoxyanilineHCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate

Product 1

HCID 13562779Ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylateYield 60.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (21.5 g) and 2-butoxyaniline (24 g) are added to pyridine (50 ml), and the mixture is refluxed with stirring for 18 hours. The reaction mixture is concentrated to dryness. The residue is recrystallized from DMF to give ethyl 1,6-dihydro-2-(2-butoxyanilino)-6-oxo-5-pyrimidinecarboxylate (20 g). M.p. 209°-211° C.

Workup

  1. temperaturethe mixture is refluxed
  2. concentrationThe reaction mixture is concentrated to dryness
  3. customThe residue is recrystallized from DMF

Sources & evidence

ORD record
ord-c6b4e61da94b46858d0e79b139946c45
Source dataset
uspto-grants-1987_05
Patent number
US04666915

Linked notes

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