Ethyl Acetate → 2-Benzoyl-pyrimidine-5-carbonitrile

HRID 2381957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381957
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O.C[C:29]([N:31](C)C)=O>[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]([C:5]1[N:4]=[CH:3][C:2]([C:29]#[N:31])=[CH:7][N:6]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 67360359(5-Bromo-pyrimidine-2-yl)-phenyl-methanone

Produkt 1

HCID 685564332-Benzoyl-pyrimidine-5-carbonitrileAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 161067Potassium ferrocyanide trihydrateKatalysatorHCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

(5-Bromo-pyrimidine-2-yl)-phenyl-methanone (1.6 g, 6.08 mmol) is dissolved in dimethylacetamide (20 mL), and potassium hexacyanoferrate(II) trihydrate (0.57 g, 1.34 mmol) is added, followed by Na2CO3 (0.64 g, 6.08 mmol), and palladium (II) acetate (68 mg, 0.3 mmol). The mixture is heated to 150° C. under N2 for 3 h, and then cooled to rt. EtOAc (30 mL) is added and the mixture is filtered. The filtrate is washed with water (2×15 mL) and 5% aqueous NH4OH (15 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 70% EtOAc in heptane to afford 2-benzoyl-pyrimidine-5-carbonitrile (0.53 g, 42%) as a solid. MS: 210 (M+H).

Aufarbeitung

  1. temperaturecooled to rt
  2. filtrationthe mixture is filtered
  3. washThe filtrate is washed with water (2×15 mL) and 5% aqueous NH4OH (15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 70% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-853f8fc10aab41e595ebdb867dacb79f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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