(Trifluoromethyl)trimethylsilane → HCID 57785989, compound

HRID 1399117Notes

Reaction equation

HRID 1399117 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[N:27]1[C:32]2=[N:33][C:34]3[C:35](=[C:36]([CH:40]=[O:41])[CH:37]=[CH:38][CH:39]=3)[N:31]2[CH2:30][CH2:29][CH2:28]1.C[Si](C)(C)[C:44]([F:47])([F:46])[F:45]>O1CCCC1.Cl>[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[N:27]1[C:32]2=[N:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]([OH:41])[C:44]([F:47])([F:46])[F:45])[C:35]=3[N:31]2[CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 57786099HCID 57786099, compound

Product 1

HCID 57785989HCID 57785989, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium fluoride (1.0 M solution in tetrahydrofuran, 1.3 mL, 1.3 mmol) was added dropwise to a stirred solution of 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (1.50 g, 4.33 mmol) and trimethyl(trifluoromethyl)silane (1.83 g, 12.9 mmol) in tetrahydrofuran (11 mL) at 0° C., and the mixture was stirred at room temperature for 10 hr. The mixture was diluted with 1N hydrochloric acid and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (1.19 g, 2.86 mmol, 66%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a2af0313b98d473e9bd055c84615d2e0
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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