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

HRID 2381957ノート

反応式

HRID 2381957 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 685564332-Benzoyl-pyrimidine-5-carbonitrile収率 42%

試薬・触媒・溶媒 2

HCID 161067Potassium ferrocyanide trihydrate触媒HCID 167845palladium(II) acetate触媒

反応条件

温度
150 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-853f8fc10aab41e595ebdb867dacb79f
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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