Diethyl Ether → Tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate
Reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.CCOCC.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])=[CH:21][CH:20]=1.CCN(CC)CC>[Cl-].[Cl-].[Zn+2].ClCCCl.CC(O)(C)C>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])=[CH:21][CH:20]=2)[N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
2,4-Dichloro-5-(trifluoromethyl)pyrimidine (1.93 g, 8.89 mmol) was stirred in a 1:1 t-BuOH:DCE mixture (200 mL) at room temperature. A 1.0 M ZnCl2 solution in Et2O (10.2 mL, 10.2 mmol) was added cautiously and the mixture was stirred at room temperature for 20 minutes. A 1:1 t-BuOH:DCE mixture (100 mL) was added followed by tert-butyl (1-(4-aminophenyl)ethyl)carbamate (2.00 g, 8.46 mmol) and Et3N (1.42 mL, 10.2 mmol). The mixture was stirred at room temperature overnight before the volatiles were evaporated in vacuo. EtOH (30 mL) was added, the suspension was sonicated for 1 minute before the solid was filtered, washed with EtOH (10 mL) and dried in vacuo to give the title compound A80 as a cream solid (3.2 g, 91%). LCMS-C: rt 4.88 min.
Workup
- customat room temperature
- stirringThe mixture was stirred at room temperature overnight before the volatiles
- customwere evaporated in vacuo
- additionEtOH (30 mL) was added
- customthe suspension was sonicated for 1 minute before the solid
- filtrationwas filtered
- washwashed with EtOH (10 mL)
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d8c8a23f7c554cd097d6fd06c5592ac3
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238644B2
Reaction notes
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