Sodium Carbonate → 2,4-Dichloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidine

HRID 230942노트

반응식

HRID 230942 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[Cl:1][C:2]1[N:3]=[C:4]([Cl:9])[CH:5]=[C:6]([C:13]2[CH:14]=[CH:15][C:16]([F:17])=[C:11]([Cl:10])[CH:12]=2)[N:7]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 773782,4,6-TrichloropyrimidineHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 577610582,4-Dichloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

Combine 2,4,6-trichloropyrimidine (9.15 g, 0.05 mol), 3-chloro-4-fluorophenylboronic acid (8.7 g, 0.05 mol), 1,2-dimethoxyethane (300 mL), and 2M aqueous sodium carbonate (25 mL) and let stir under nitrogen for 10 minutes. Add palladium acetate (56 mg, 0.25 mmol) and PPh3 (131 mg, 0.5 mmol) and reflux the mixture for 16 hours. Evaporate, add water (100 mL), and extract twice with DCM (25 mL each). Dry the organic layer with sodium sulfate and evaporate, giving a yellow gum. The mixture is chromatographed with 20:1 hexanes/EtOAc, affording 2,4-dichloro-6-(3-chloro-4-fluoro-phenyl)-pyrimidine as a white solid.

후처리

  1. customEvaporate
  2. additionadd water (100 mL)
  3. extractionextract twice with DCM (25 mL each)
  4. dry with materialDry the organic layer with sodium sulfate
  5. customevaporate
  6. customgiving a yellow gum
  7. customThe mixture is chromatographed with 20:1 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-3bec91da9bee48d9bc65f4b58cff5aa6
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566712B2

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