Urea → Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 524697Notes

Reaction equation

HRID 524697 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].O=[C:6]([CH3:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C>[Br:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[NH:4][C:2](=[O:3])[NH:1]1

Participants

7

Reactant 5

HCID 1176UreaHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8868Ethyl AcetoacetateHCID 27733192-Bromo-4-fluorobenzaldehyde

Product 1

HCID 90043988Ethyl 4-(2-bromo-4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of urea (2.90 g, 48 mmol), ethyl 3-oxobutanoate (5.22 g, 40 mmol), 2-bromo-4-fluorobenzaldehyde (8.12 g, 40 mmol), chlorotrimethylsilane (3.75 g, 35 mmol) and sodium iodide (4.85 g, 35 mmol) in anhydrous acetonitrile (50 mL) was stirred at 25° C. for 12 hours in the dark. The mixture was filtered and the filter cake was washed with a little acetonitrile to give the title compound as a white solid (5.72 g, 40%). The compound was characterized by the following spectroscopic data:

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with a little acetonitrile

Sources & evidence

ORD record
ord-dd33bbb4c0c740e6930fd9c9e0dda9bd
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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