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Diisopropyl Ether → 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine

HRID 2284714
ノート
印刷プレビュー

反応式

HRID 2284714 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(OC(C)C)(C)C>O1CCCC1.C(O)C.O.NN>[NH2:24][CH2:23][CH2:22][CH2:21][C:20]#[C:19][C:12]1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[N:14][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:10][CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 7914Diisopropyl EtherHCID 900522652-(5-(2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione

生成物 1

HCID 900522675-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine収率 61.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 8028Tetrahydrofuran
溶媒
HCID 24654Hydrazine hydrate (1:1)溶媒

実験手順

To a solution of 2-(5-(2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (F3, 2.51 g) in tetrahydrofuran (20 mL) and ethanol (10 mL), hydrazine monohydrate (5.1 mL) was added at room temperature, and the mixture was stirred for 10 minutes under reflux by heating. To the reaction mixture, ethanol (10 mL) was added, and the mixture was stirred at room temperature for 3 hours and 20 minutes. To the reaction mixture, diisopropyl ether was added, the insoluble matter was removed by filtration, and then water was added to the filtrate. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 5-(5-amino-1-pentyn-1-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (F4, 1.10 g) as white solid.

後処理

  1. temperatureunder reflux
  2. temperatureby heating
  3. stirringthe mixture was stirred at room temperature for 3 hours and 20 minutes
  4. customthe insoluble matter was removed by filtration
  5. additionwater was added to the filtrate
  6. customThe organic layer was separated
  7. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-3904b00c24db4d33a285b20201c6ad5b
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145415B2

反応ノート

読み込み中…

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