Chlorine → 1-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

HRID 750485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750485
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH:9]([OH:11])[CH3:10])=[CH:4][N:3]=1.CC1(C)N([O])C(C)(C)CCC1.C(=O)(O)[O-].[Na+].ClCl>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](=[O:11])[CH3:10])=[CH:4][N:3]=1

Komponenten

9

Edukt 4

HCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 151416481-(2,4-Dichloropyrimidin-5-yl)ethan-1-ol

Produkt 1

HCID 212747081-(2,4-Dichloropyrimidin-5-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred suspension of 1-(2,4-dichloro-pyrimidin-5-yl)-ethanol (Example 20, 1.00 g, 5.2 mmol) in a mixture of methylene chloride (30 mL), THF (8 mL) and water (2 mL), tetrabutylammonium chloride (Aldrich, 50 mg, 0.15 mmol), TEMPO (Aldrich, 9 mg, 0.05 mmol) and sodium bicarbonate (208 mg, 2.48 mmol) were added and the mixture was cooled to 0° C. To the stirred mixture, colorex (Aldrich; active Cl2, 10-13%; 3.75 mL) was added and the mixture was stirred for 2 hours at 0° C. Water (10 mL) was added and the organic layer was separated and dried over sodium sulfate. Removal of solvent gave an oil which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield a colorless oil. 232 mg, 23%. MS (M+H)+, 191.

Aufarbeitung

  1. additionwere added
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvent
  5. customgave an oil which
  6. customwas purified by silica gel chromatography (1% MeOH/CH2Cl2)
  7. customto yield a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-08afe15dbd4d464195433ac037f25b92
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405220B2

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