Hydrochloric Acid → 4-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine

HRID 526056ノート

反応式

HRID 526056 の反応式
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:17]=[C:18]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=4)[C:19]4[S:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1>C(O)C.[Fe]>[NH2:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[O:25][C:18]1[C:19]2[S:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:5][CH2:4][N:3]([CH3:2])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)[N:17]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 68001679N-(4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine

生成物 1

HCID 895474154-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine収率 67.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 702Ethanol溶媒2 回

反応条件

温度
100 °C

実験手順

Iron (27.1 mmol) and 12 N HCl aqueous solution (2.17 mmol) were diluted with 50% ethanol aqueous solution (30 mL), followed by stirring at 100° C. for 10 min. The compound (5.42 mmol) obtained in Step 4 was dissolved in 50% ethanol aqueous solution (30 mL) and then added to the reaction flask in which iron was activated, followed by stirring at 100° C. for 1 hour. After the reaction was complete, the reaction mixture was filtered with celite to remove iron, and the filtrate was distilled under a reduced pressure. The residue was distilled with dichloromethane and washed with sat. NaHCO3 aqueous solution. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio)) to obtain the title compound (yield: 67.8%).

後処理

  1. stirringby stirring at 100° C. for 1 hour
  2. filtrationthe reaction mixture was filtered with celite
  3. customto remove iron
  4. distillationthe filtrate was distilled under a reduced pressure
  5. distillationThe residue was distilled with dichloromethane
  6. washwashed with sat. NaHCO3 aqueous solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure
  10. customThe residue was separated by column chromatography (dichloromethane:methanol=10:1 (volume ratio))

出典と根拠

ORDレコード
ord-e3bfc2d4cf504b01812123a204c00906
出典データセット
uspto-grants-2016_05
特許番号
US09345719B2

反応ノート

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