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Methanol → 2-(4-Fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazine

HRID 2233087
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2233087
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20](SC)[N:19]=2)=[CH:4][CH:3]=1.O[O:27][S:28]([O-:30])=O.[K+].[CH3:32]O>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:28]([CH3:32])(=[O:30])=[O:27])[N:19]=2)=[CH:4][CH:3]=1
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Komponenten

6

Edukt 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 574387482-(4-Fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 588695482-(4-Fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (Example #F.1A; 8.58 g, 24.4 mmol) in MeOH (200 mL) and DCM (200 mL) at ambient temperature was added Oxone® (30.0 g, 48.8 mmol) in water (100 mL) to form a suspension. After about 20 h of stirring the layers were separated. The aqueous layer was washed with DCM (3×30 mL). Combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid, which was purified via FCC using EtOAc as an eluent. The product-containing fractions were combined and concentrated under reduced pressure to give a white solid (6.5 g) that was recrystallized in IPA (700 mL) to yield the title compound (3.6 g) after filtration. Additional product was observed in the filtrate. (3.6 g, 38% yield): LC/MS (Table 1, Method b) Rt=1.7 min; MS m/z: 384.1 (M+H)+.

Aufarbeitung

  1. customat ambient temperature
  2. customto form a suspension
  3. customwere separated
  4. washThe aqueous layer was washed with DCM (3×30 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto yield a yellow solid, which
  9. customwas purified via FCC
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a6e2710e4b114fb2b5bc36703dfa0892
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709468B2

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