Trifluoroacetic acid → HCID 90402690, Verbindung

HRID 2200601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200601
COC1C=CC(C[N:8]2[C:16](=[O:17])[C:15]3[N:14]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=4)[C:13]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=4)=[N:12][C:11]=3[N:10]([CH3:38])[C:9]2=[O:39])=CC=1.OS(C(F)(F)F)(=O)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:38][N:10]1[C:11]2[N:12]=[C:13]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]([F:37])([F:36])[F:35])[CH:28]=3)[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[C:15]=2[C:16](=[O:17])[NH:8][C:9]1=[O:39]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 90402978HCID 90402978, Verbindung

Produkt 1

HCID 90402690HCID 90402690, VerbindungAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-methoxybenzyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (120 mg, 0.212 mmol) in DCM (1.4 mL) was added triflic acid (0.7 mL) and TFA (0.7 mL). The reaction was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with saturated NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by silica gel chromatography eluting with petroleum/ethyl acetate (10:1 to 1:1) to give 3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (60 mg, 63.5% yield) as white solid. LCMS MH+ 446.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with saturated NaHCO3 and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with petroleum/ethyl acetate (10:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-58c0297747694c4a822a31c988b79ce6
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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