Ethyl Bromide → 4-[3-ethyl-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-6,7-dihydro-4H-cyclopenta[d]pyrimidin-4-yl]-3-methylsulfonylbenzonitrile

HRID 927238Notes

Reaction equation

HRID 927238 reaction equation
Br[CH2:2][CH3:3].[O:4]=[C:5]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]2[CH2:21][CH2:22][C:23](=[O:24])[C:8]=2[CH:7]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=2[S:33]([CH3:36])(=[O:35])=[O:34])[NH:6]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:2]([N:6]1[CH:7]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=2[S:33]([CH3:36])(=[O:34])=[O:35])[C:8]2[C:23](=[O:24])[CH2:22][CH2:21][C:9]=2[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[C:5]1=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 903107954-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-4-yl)-3-(methylsulfonyl)benzonitrile

Product 1

HCID 903110374-[3-ethyl-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-6,7-dihydro-4H-cyclopenta[d]pyrimidin-4-yl]-3-methylsulfonylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoethane (20 μL, 0.27 mmol) is added to a solution of 4-(2,5-dioxo-1-(3-(trifluoro-methyl)phenyl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)-3-(methyl-sulfonyl)benzonitrile (example 10, 60 mg, 0.11 mmol based on 90% purity) and cesium carbonate (74 mg, 0.23 mmol) in N,N-dimethylformamide (2.0 mL). The mixture is stirred at room temperature over night and purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 23 mg; ESI mass spectrum [M+H]+=504; Retention time HPLC: 0.86 min (005_CA01).

Workup

  1. custompurified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom0.86 min (005_CA01)

Sources & evidence

ORD record
ord-c65a51317cfe43ab808a38ea5c8f6dc7
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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