2-Chloro-4-(trifluoromethyl)pyrimidine → N-(3-bromo-5-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 595171Notes

Reaction equation

HRID 595171 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=1.[Br:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([Cl:26])[CH:25]=1)[NH2:22]>C1COCC1.[Cl-].[NH4+]>[Br:18][C:19]1[CH:20]=[C:21]([NH:22][C:8]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1

Participants

6

Reactant 3

HCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 30847093-Bromo-5-chloroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 117670750N-(3-bromo-5-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium tert-butoxide (750 mg, 6.69 mmol) was added to a solution of 2-chloro-4-(trifluoromethyl)pyrimidine (406 mg, 2.23 mmol) and 3-bromo-5-chloroaniline (460 mg 2.23 mmol) in THF (20 mL) at 0° C. under a nitrogen atmosphere. The mixture was stirred at 70° C. for 12 hours. The mixture was then diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by chromatography on silica gel to give N-(3-bromo-5-chlorophenyl)-4-(trifluoromethyl)pyrimidin-2-amine MS ESI calc'd. for C11H7BrClF3N3 [M+H]+ 352 and 354. found 352 and 354.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8b4fdbe0aac04c71b9827bb84a4fa6fb
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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