(Trifluoromethyl)benzene → HCID 86685393, compound

HRID 570735Notes

Reaction equation

HRID 570735 reaction equation
[CH2:1]([S:3][C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[C:8]=2[N:9]=1)[CH3:2].F[C:29](C1C=CC=CC=1)(F)F.F[B-](F)(F)F.C[O+](C)C>C(OCC)(=O)C>[CH2:1]([S:3][C:4]1[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH3:29])[C:8]=2[N:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7368(Trifluoromethyl)benzeneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 68015322HCID 68015322, compound

Product 1

HCID 86685393HCID 86685393, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (40 mg) and (trifluoromethyl)benzene (10 ml) was added trimethyloxonium tetrafluoroborate (22 mg) at room temperature, and the reaction mixture was heated under reflux for 3 hr, allowed to be cooled to room temperature, and diluted with ethyl acetate. The reaction mixture was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and recrystallized from a mixed solvent of ethyl acetate/hexane to give the title compound (16 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 3 hr
  3. washThe reaction mixture was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customrecrystallized from a mixed solvent of ethyl acetate/hexane

Sources & evidence

ORD record
ord-4c0ddd43bbff4c569b9d3280b6276336
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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