Boron trifluoride etherate → HCID 178506246, compound

HRID 1774611Notes

Reaction equation

HRID 1774611 reaction equation
B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[C:22]([C:24]3[N:25](COCC[Si](C)(C)C)[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)[N:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]>C(Cl)Cl.CCCCCCC>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[C:22]([C:24]3[NH:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)[N:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

5

Reactant 2

HCID 8000Boron trifluoride etherateHCID 71240810HCID 71240810, compound

Product 1

HCID 178506246HCID 178506246, compoundYield 107.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron trifluoride diethyl etherate (0.16 ml, 1.3 mmol) was added dropwise to a cool (0° C.), stirred solution of 4-(3,4-dichloro-phenyl)-6-[4-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-pyrimidine (0.064 g, 0.13 mmol) in DCM (2 ml) under a nitrogen atmosphere. The mixture was stirred at this temperature for 10 minutes before being allowed to warm to room temperature and stirred overnight. The solution was diluted with heptane (5 ml) and the resulting precipitate was collected by filtration and dried under vacuum before being purified by prep HPLC to give the title compound (0.05 g, 15% yield) as a white powder.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried under vacuum
  5. custombefore being purified by prep HPLC

Sources & evidence

ORD record
ord-c28e3f89c7274c4095418b8acdcd6063
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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