Ethyl acetate hexane → N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamine

HRID 1482665ノート

反応式

HRID 1482665 の反応式
[F:1][C:2]1[C:3]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[H][H].CCCCCC.C(OCC)(=O)C>CO.[Pd]>[NH2:29][C:25]1[CH:24]=[C:23]([NH:22][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:11][CH:10]=3)[N:4]=2)[CH:28]=[CH:27][CH:26]=1

参加物

6

反応物 3

HCID 21226206Ethyl acetate hexaneHCID 867243285-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86724329N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamine収率 80.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a suspension of Pd/C (0.2 g) in methanol (20 mL), 5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)-N4-(3-nitrophenyl)pyrimidine-2,4-diamine (0.40 g) was added under nitrogen atmosphere into the autoclave at room temperature. Hydrogen pressure (70 psi) was applied and the reaction mixture was stirred overnight at room temperature. The reaction was monitored on TLC using hexane:ethyl acetate (4:6) as mobile phase. After completion, the reaction mixture was filtered using Celite and the filter cake was washed with methanol. The combined filtrate was concentrated under reduced pressure at 40° C. to give 0.3 g of N4-(3-aminophenyl)-5-fluoro-N2-(4-((2-methoxyethoxy)methoxy)phenyl)pyrimidine-2,4-diamine as a solid.

後処理

  1. additionwas added under nitrogen atmosphere into the autoclave at room temperature
  2. filtrationAfter completion, the reaction mixture was filtered
  3. washthe filter cake was washed with methanol
  4. concentrationThe combined filtrate was concentrated under reduced pressure at 40° C.

出典と根拠

ORDレコード
ord-7f3e97ce688c461ab2b9fabbbd30332f
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

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