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3-Fluoroaniline → 4-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine

HRID 913290
ノート
印刷プレビュー

反応式

HRID 913290 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]([CH3:19])[CH2:16][S:17][CH3:18])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]([CH3:19])[CH2:16][S:17][CH3:18])[N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:25]=[CH:26][CH:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 97423-FluoroanilineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 866467764-(2-chloro-4-pyridinyl)-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine2 回

生成物 1

HCID 673888194-[2-[(3-fluorophenyl)amino]-4-pyridinyl]-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a solution of 4-(2-chloro-4-pyridinyl)-N-[1-methyl-2-(methylthio)ethyl]-2-pyrimidinamine (i.e., the product of Step C) (150 mg, 0.5 mmol) in toluene (6.0 mL) was added 3-fluoroaniline (108 μL, 1.1 mmol), palladium(II) acetate (24 mg, 0.12 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene ((±)-BINAP) (40 mg, 0.06 mmol) and cesium carbonate (700 mg, 2.2 mmol); the resulting mixture was stirred at 110° C. for 13 h. The mixture was allowed to cool and silica gel (300 mg) was added. The excess solvent was removed under reduced pressure, and the resulting solid was chromatographed on silica gel eluted with 5% to 60% ethyl acetate in hexanes to give 60 mg of the title compound as a yellow solid, m.p. 104-107° C.

後処理

  1. temperatureto cool
  2. additionsilica gel (300 mg) was added
  3. customThe excess solvent was removed under reduced pressure
  4. customthe resulting solid was chromatographed on silica gel
  5. washeluted with 5% to 60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-1c165ee1b2534e5dbcda429e26298761
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08026359B2

反応ノート

読み込み中…

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