Triphenylarsine → 4-Chloro-2-(6-chloropyrimidin-4-yl)aniline

HRID 625378ノート

反応式

HRID 625378 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:23]2[CH:24]=[C:19]([Cl:18])[N:20]=[CH:21][N:22]=2)[CH:3]=1

参加物

8

反応物 4

HCID 11773TriphenylarsineHCID 62657Potassium Phosphate, TribasicHCID 709434,6-DichloropyrimidineHCID 177502054-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 867059594-Chloro-2-(6-chloropyrimidin-4-yl)aniline

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
75 °C

実験手順

Into a 250-mL round bottom flask, was placed a solution of 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (3 g, 11.83 mmol, 1.00 equiv) in dioxane (120 mL), water (20 mL), 4,6-dichloropyrimidine (4.4 g, 29.53 mmol, 2.50 equiv), triphenylarsine (360 mg, 1.18 mmol, 0.10 equiv), K3PO4 (3.8 g, 17.90 mmol, 1.50 equiv), Pd(PPh3)2Cl2 (390 mg, 0.56 mmol, 0.05 equiv). The resulting solution was stirred for 3 h at 75° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50˜1:10). This resulted in 1.5 g (53%) of 4-chloro-2-(6-chloropyrimidin-4-yl)benzenamine as a yellow solid.

後処理

  1. customInto a 250-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 1.5 g (53%) of 4-chloro-2-(6-chloropyrimidin-4-yl)benzenamine as a yellow solid

出典と根拠

ORDレコード
ord-6d2a8c8f77964960bb0658629309fb32
出典データセット
uspto-grants-2016_04
特許番号
US09301951B2

反応ノート

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