Tetrahydrofuran → 2-(2-Ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline

HRID 1775264Notes

Reaction equation

HRID 1775264 reaction equation
C[Mg]Br.[CH2:4]1COCC1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=2)[N:13]=[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][CH2:31][CH3:32])[N:11]=1.CN1C(=O)CCC1>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O.C(OCC)(=O)C>[CH2:31]([S:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:12]1[N:11]=[C:10]([CH3:4])[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])=[CH:17][CH:18]=2)[N:13]=1)[CH3:32]

Participants

8

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 13387N-methyl-2-pyrrolidoneHCID 1182058194-Chloro-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazolineHCID 178418573HCID 178418573, compound

Product 1

HCID 1182058222-(2-Ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline

Reagents, catalysts & solvents 3

HCID 5483663Ferric acetylacetonateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.1 ml of methylmagnesium bromide (a 1 M THF solution) was added to a mixture of 380 mg of 4-chloro-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline, 72 mg of iron(III) acetylacetonate, 8 ml of THF and 0.8 ml of NMP, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added to the reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, combined with the organic layer of the filtrate, sequentially washed with 0.5 N hydrochloric acid, water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 123 mg of 2-(2-ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline (Compound of Present Invention 13).

Workup

  1. filtrationthe mixture was filtered
  2. extractionThe aqueous layer of the filtrate was extracted with ethyl acetate
  3. washsequentially washed with 0.5 N hydrochloric acid, water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84332b6f42f149e5ab47abb8b7183b28
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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