Thionyl Chloride → 2-(5-Bromo-2-fluorophenyl)-4-Chloropteridine

HRID 928264

Reaktionsgleichung

Reaktionsgleichung von HRID 928264
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:23])=[C:10]([C:12]2[NH:21][C:20](=O)[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[N:13]=2)[CH:11]=1>C(Cl)(Cl)Cl.CN(C=O)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:23])=[C:10]([C:12]2[N:21]=[C:20]([Cl:3])[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[N:13]=2)[CH:11]=1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 1361099582-(5-Bromo-2-fluoro-phenyl)-3H-pteridin-4-one

Produkt 1

HCID 577423812-(5-Bromo-2-fluorophenyl)-4-ChloropteridineAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Thionyl chloride (371 mg, 3.11 mmol) was added to the stirred suspension of 2-(5-bromo-2-fluorophenyl)pteridin-4-one 104 (200 mg, 0.623 mmol) in chloroform (5 mL) and dry DMF (100 μL). The reaction mixture was refluxed under nitrogen for 1 h (starting material gone by HPLC). The solvent was removed in vacuo. Then the residue was triturated in Et2O and filtered off to give 210 mg of the title product 106 as a yellow solid (LCMS analysis).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed under nitrogen for 1 h (starting material gone by HPLC)
  2. customThe solvent was removed in vacuo
  3. customThen the residue was triturated in Et2O
  4. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-66c332a926ac4642aa5cca4f7bd70f04
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290502B2

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