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

HRID 2381957노트

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HRID 2381957 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 161067Potassium ferrocyanide trihydrate촉매HCID 167845palladium(II) acetate촉매

반응 조건

온도
150 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-853f8fc10aab41e595ebdb867dacb79f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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