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Potassium Iodide → 2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-one

HRID 2278540
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278540
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[N:5]=[C:4]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[C:17]([F:22])[CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[N:3]=1.[I-].[K+].C(#N)C.C[Si](C)(C)Cl>CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:10][C:11]([N:13]2[C:21]3[C:16](=[C:17]([F:22])[CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[NH:5][C:6](=[O:8])[CH:7]=1
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Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 866992651-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone

Produkt 1

HCID 1363786742-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-chloro-3H-pyrimidin-4-oneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2 g of 2-(4-chloro-6-methoxypyrimidin-2-yl)-1-(4-fluoro-2,3-dihydroindol-1-yl)ethanone (example 17b, step 1b), potassium iodide (3.1 g), 30 ml of acetonitrile and 2.03 g of trimethylchlorosilane are placed in a reactor suitable for microwave-heating. The reactor is closed and irradiated for 30 minutes at 100° C. and then left overnight at A.T. The reaction medium is diluted with EtOAc and then washed twice with water and then with brine. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated. The product obtained is chromatographed on silica. Elution is then carried out with dichloromethane/methanol (from 100/0 to 95/5). The fractions containing the expected product are evaporated under reduced pressure. The compound obtained is triturated from methanol, filtered and dried. 2-(4-Chloro-6-oxopyrimidin-2-yl)-1-(4-fluoro-2,3-dihydroindol-1-yl) ethanone is isolated (1.13 g); yield=59% (LCMS ES+ retention time Tr (min)=1.04; [M+H]+: m/z 308).

Aufarbeitung

  1. temperaturesuitable for microwave-heating
  2. customThe reactor is closed
  3. customirradiated for 30 minutes at 100° C.
  4. washwashed twice with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe product obtained
  9. customis chromatographed on silica
  10. washElution
  11. additionThe fractions containing the expected product
  12. customare evaporated under reduced pressure
  13. customThe compound obtained
  14. customis triturated from methanol
  15. filtrationfiltered
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-180d77540ffa4ac6a5e6a73e1478be1d
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133168B2

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