Hydrochloric Acid → Ethyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[4-fluorophenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

HRID 2246387Notes

Reaction equation

HRID 2246387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].O=[C:23]([CH3:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl>C1COCC1>[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:10])[NH:11]2)=[CH:16][CH:15]=1)#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 126124-FluorophenylureaHCID 660424-Cyanobenzaldehyde

Product 1

HCID 58674268Ethyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[4-fluorophenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

154 mg (1.0 mmol) N-[4-fluorophenyl]urea, 101 mg (0.77 mmol) 4-cyanobenzaldehyde, and 100 mg (0.77 mmol) ethyl 3-oxobutanoate are suspended in 2 ml of THF, and catalytic amounts of concentrated hydrochloric acid are added. The mixture is stirred at reflux for 18 hours. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate as eluent.

Workup

  1. temperatureat reflux for 18 hours
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-04fd94625b0f4a94997ccc73ef535788
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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