1-(Bromomethyl)-4-(trifluoromethoxy)benzene → N-[2-(3-bromo-4-methoxyphenyl)ethyl]-5-isopropyl-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13]2[N:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:22][C:23]([F:34])([F:33])[O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][C:23]([F:22])([F:33])[F:34])=[CH:26][CH:27]=2)[C:13]2[N:14]=[CH:15][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:17][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-[2-(3-bromo-4-methoxyphenyl)ethyl]-5-isopropylpyrimidin-2-amine (157 mg; 0.45 mmol) in dry THF was treated under nitrogen with KtBuO (75 mg; 0.67 mmol). After stirring for 15 minutes, 4-trifluoromethoxybenzyl bromide (171 mg; 0.67 mmol) was added and stirred for 30 minutes. The reaction was quenched by addition of an aqueous solution of NaHSO4 and extracted with dichloromethane. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford N-[2-(3-bromo-4-methoxyphenyl)ethyl]-5-isopropyl-N-[4-(trifluoromethoxy)benzyl]pyrimidin-2-amine as an oil in moderate yield, which was used in the next step without further purification
Workup
- stirringstirred for 30 minutes
- customThe reaction was quenched by addition of an aqueous solution of NaHSO4
- extractionextracted with dichloromethane
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7b056ede25084fdca8a61758aef95a11
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07319104B2
Reaction notes
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