Water → 4-(4-Bromophenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

HRID 927191Notes

Reaction equation

HRID 927191 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17]([NH:21][C:22]2[CH2:26][CH2:25][C:24](=[O:27])[CH:23]=2)[CH:18]=[CH:19][CH:20]=1.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:9][C:10](=[O:11])[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:28])[F:29])[CH:16]=3)[C:22]3[CH2:26][CH2:25][C:24](=[O:27])[C:23]2=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzeneHCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-one

Product 1

HCID 903109024-(4-Bromophenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (14.7 g, 47.6 mmol) in dichloromethane (100 mL) is added to a solution of 3-(3-(trifluoromethyl)phenylamino)-cyclopent-2-enone (11.0 g, 45.6 mmol) in dichloromethane (100 mL) and the mixture is heated at reflux for 1.5 hours. Water is added, and the phases are extracted twice with dichloromethane. The combined organic layers are concentrated and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 4:1 to ethyl acetate). Yield: 7.5 g; ESI mass spectrum: ESI mass spectrum: [(79Br)-M+H]+=451, [(81Br)-M+H]+=453; Retention time HPLC: 1.15 min (V012_S01).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 1.5 hours
  3. extractionthe phases are extracted twice with dichloromethane
  4. concentrationThe combined organic layers are concentrated
  5. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 4:1 to ethyl acetate)
  6. custom1.15 min (V012_S01)

Sources & evidence

ORD record
ord-7df1f7a3829c426980bb7df805e1562a
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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