Urea → Methyl 4-(4-fluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 227707Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8][CH3:9])=[O:7].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[NH2:20][C:21]([NH2:23])=[O:22].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1.O>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:3][O:2][CH3:1])[NH:23][C:21](=[O:22])[NH:20]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 4-(methyloxy)-3-oxobutanoate (2.0 g, 13.69 mmol, 1 equiv), 4-Fluorobenzaldehyde (1.7 g, 13.69 mmol, 1 equiv), urea (1.64 g, 27.34 mmol, 2 equiv), and ytterbium triflate (854 mg, 1.37 mmol, 0.1 equiv) were combined in Toluene (3 mL) and heated to 100° C. in a sealed tube for three hours. The residue was diluted with 10 mL of water and extracted with EtOAc (10 mL). The organic layer was washed with brine and concentrated en vacuo to yield 4.03 g of the title compound as a light yellow oil (100%). MS (ES+) m/e 295 [M+H]+

Workup

extractionextracted with EtOAc (10 mL)
washThe organic layer was washed with brine
concentrationconcentrated en vacuo

Sources & evidence

ORD record: ord-fa72a0ad3f224cd894286aa0c4c2f465
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560467B2

Reaction notes

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