Hydrochloric Acid → Ethyl 1,6-dihydro-2-[2-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate

HRID 979141Notes

Reaction equation

O1CCN([CH:7]=[C:8]([C:14](OCC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])CC1.[CH3:19][CH:20]([CH3:33])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30]([NH2:32])=[NH:31].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[CH3:19][CH:20]([CH3:33])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30]1[NH:32][C:14](=[O:15])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Diethyl morpholinomethylenemalonate (20.0 g) is added to a solution of N-[2-(2-methylpropoxy)phenyl]guanidine (16.1 g) and potassium carbonate (21.5 g) in ethanol (40 ml) and water (40 ml), and the mixture is heated with stirring at 60° C. for 3 hours. After the reaction is completed, water (100 ml) is added to the reaction mixture with stirring under water-cooling, and the mixture is acidified to pH 3 with 10% aqueous HCl. The resulting precipitate is collected by filtration and dissolved in chloroform (300 ml). The chloroform layer is washed with water twice, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue is recrystallized from DMF to give ethyl 1,6-dihydro-2-[2-(2-methylpropoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (16.0 g). M.p. 175°-177° C.

Workup

temperaturethe mixture is heated
stirringwith stirring under water-
temperaturecooling
filtrationThe resulting precipitate is collected by filtration
dissolutiondissolved in chloroform (300 ml)
washThe chloroform layer is washed with water twice
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue is recrystallized from DMF

Sources & evidence

ORD record: ord-d9f49ecd4a5045489af10be0157fed2f
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04666915

Reaction notes

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