Ethyl Acetate → HCID 68556433, compound

HRID 2381957Notes

Reaction equation

HRID 2381957 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 68556433HCID 68556433, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 161067Potassium ferrocyanide trihydrateCatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
150 °C

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-853f8fc10aab41e595ebdb867dacb79f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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