Urea → HCID 66955131, compound

HRID 2088443Notes

Reaction equation

HRID 2088443 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(O[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])C.[NH2:20][C:21]([NH2:23])=[O:22]>C(#N)C>[CH2:18]([O:17][C:15]([C:14]1[CH:6]([C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[NH:20][C:21](=[O:22])[NH:23][CH:13]=1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 221780Ethyl 3-ethoxy-2-propenoate

Product 1

HCID 66955131HCID 66955131, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Fluoro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester was prepared using the Biginelli reaction following the procedure reported in WO 2007/101213). Briefly, to a solution of p-fluorobenzaldehyde (7.5 mL) in 200 mL acetonitrile was added ethyl 3-ethoxyacrylate (10.7 mL), urea (5.0 g) and freshly dried SiO2—NaHSO4 (3.7 g). The solution was heated at reflux for 18 hours, then cooled and poured into ice water. The precipitate was recovered by filtration and air-dried to yield 4-(4-fluoro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (18.8 g).

Workup

  1. custom4-(4-Fluoro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester was prepared
  2. customthe Biginelli reaction
  3. temperatureThe solution was heated
  4. temperatureat reflux for 18 hours
  5. temperaturecooled
  6. filtrationThe precipitate was recovered by filtration
  7. customair-dried

Sources & evidence

ORD record
ord-fb93ef1640084e8d9436aae400ef23c6
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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