Potassium Carbonate → Ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxylate

HRID 1627706Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (1.2 g) [see J. Med. Chem., 43, 3995 (2000)], 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.5 g), and potassium carbonate (0.7 g) were added to N,N-dimethylformamide (50 mL) and the mixture was heated at 100° C. for 5 hours. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (2.4 g, 95%).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was then purified by a silica gel chromatography

Sources & evidence

ORD record: ord-26eb9bb2e7a14447838a3ed095c5811e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785647B2

Reaction notes

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