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

HRID 625378노트

반응식

HRID 625378 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d2a8c8f77964960bb0658629309fb32
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

반응 노트

불러오는 중…