(3-Trifluoromethylphenyl)urea → 4-{6-Methyl-5-(4-morpholinylcarbonyl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

HRID 2246390Notes

Reaction equation

HRID 2246390 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[N:25]1([C:31](=[O:36])[CH2:32][C:33](=O)[CH3:34])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C1COCC1>[CH3:34][C:33]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)[C:10](=[O:11])[NH:12][CH:21]([C:20]2[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=2)[C:32]=1[C:31]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:36]

Participants

5

Reactant 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 855504-(1,3-Dioxobutyl)morpholine

Product 1

HCID 586742544-{6-Methyl-5-(4-morpholinylcarbonyl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.73 mmol) N-[3-(trifluoromethyl)phenyl]urea, 96 mg (0.73 mmol) 4-cyanobenzaldehyde, 63 mg (0.37 mmol) 4-(4-morpholinyl)-4-oxo-2-butanone and 220 mg polyphosphoric acid ethyl ester are suspended in 3 ml of THF. 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 dichloromethane/methanol 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 dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-1689d0b79c274e62bd1312c0cd4e5b53
Source dataset
uspto-grants-2010_03
Patent number
US07687510B2

Reaction notes

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