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

HRID 230942ノート

反応式

HRID 230942 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3bec91da9bee48d9bc65f4b58cff5aa6
出典データセット
uspto-grants-2009_07
特許番号
US07566712B2

反応ノート

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