Methanol → Ethyl 3-{4-hydroxy-6-oxo-2-[(E)-2-phenylethenyl]-1,6-dihydro-5-pyrimidinyl}propanoate
Reaction equation
[CH:1]([C:13]([O:15]C)=O)([C:9]([O:11]C)=O)[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:17]1(/[CH:23]=[CH:24]/[C:25](=[NH:27])[NH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C[O-].[Na+].CO>CCO>[OH:15][C:13]1[N:26]=[C:25](/[CH:24]=[CH:23]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:27][C:9](=[O:11])[C:1]=1[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Ethyl 1,1-dimethyl 1,1,3-propanetricarboxylate (1.65 g, 7.11 mmol) and (2E)-3-phenyl-2-propenimidamide (1.04 g, 7.11 mmol) were combined in EtOH (36 mL). Triethylamine (1.98 mL, 14.2 mmol) was added and the solution was heated at reflux for 3 h with no change based on LCMS. The solution was cooled to room temperature and treated with NaOMe in MeOH (1.0 mL, 5.33 mmol, 25% wt solution) and the solution was refluxed for an additional 4 h. Another portion of NaOMe in MeOH (1.0 mL, 5.33 mmol, 25% wt solution) was added and the solution was refluxed for 16 h. After this time, a yellow precipitate had formed which was filtered off. The mother liquor was acidified to pH2 with 1N HCl, and the solution was concentrated under vacuum. The resulting material was combined with the yellow solid and used without further purification.
Workup
- temperaturethe solution was heated
- temperatureat reflux for 3 h with no change
- temperaturethe solution was refluxed for an additional 4 h
- temperaturethe solution was refluxed for 16 h
- customAfter this time, a yellow precipitate had formed which
- filtrationwas filtered off
- concentrationthe solution was concentrated under vacuum
- customused without further purification
Sources & evidence
- ORD record
- ord-d00b5518438f4d2a9aa5e8bfe439c582
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709483B2
Reaction notes
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