Sodium Carbonate → 4-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

HRID 28569

反応式

HRID 28569 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH2:21][CH3:22])=[C:15](B(O)O)[CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.C(COC)OC>[Cl:8][C:6]1[CH:7]=[C:2]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH3:22])[N:3]=[C:4]([NH2:9])[N:5]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 655222-Amino-4,6-dichloropyrimidineHCID 37008365-Chloro-2-ethoxyphenylboronic acid

生成物 1

HCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine収率 73.3%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 180Acetone溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of 4,6-dichloro-pyrimidin-2-ylamine (0.50 g, 3.0 mmol), 5-chloro-2-ethoxy-phenyl boronic acid (0.61 g, 3.0 mmol), palladium (II) acetate (0.10 g, 0.46 mmol), and triphenylphosphine (0.24 g, 0.91 mmol) was added a solution of sodium carbonate (1.6 g, 15.2 mmol) in water (5 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere at room temperature for 3.5 hours. Acetone (20 ml) was added and the mixture was filtered through a pad of celite under suction. The filtrated was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.625 g, 73% yield) as a white powder.

後処理

  1. filtrationthe mixture was filtered through a pad of celite under suction
  2. concentrationThe filtrated was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-582a73f2ba0f47c68b8c414e243374b1
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

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