2-Amino-1-phenylpropan-1-ol hydrochloride → alpha-[1-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]ethyl]benzenemethanol

HRID 275009

反応式

HRID 275009 の反応式
[C:1]1([N:7]2[C:11]3=[N:12][C:13]([Cl:17])=[N:14][C:15](Cl)=[C:10]3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][CH:19]([NH2:28])[CH:20]([OH:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.Cl.[OH-].[K+]>C(O)C.O>[C:1]1([N:7]2[C:11]3=[N:12][C:13]([Cl:17])=[N:14][C:15]([NH:28][CH:19]([CH:20]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[OH:27])[CH3:18])=[C:10]3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 90652-Amino-1-phenylpropan-1-ol hydrochlorideHCID 14797Potassium HydroxideHCID 47371094,6-dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

生成物 1

HCID 53841157alpha-[1-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]ethyl]benzenemethanol収率 90%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

390 mg of 1-phenyl-4,6-dichloropyrazolo[3,4-d]pyrimidine was suspended in 15 ml 95% ethanol. 828 mg norephedrine HCl was dissolved in 100 ml H2O, made basic with 10% KOH, and the free base extracted with 100 ml ether. The organic was dried over MgSO4, filtered, and concentrated to yield an oil which was added to the stirred reaction. After 4 hours the solution became clear and the solvent was removed under vacuum. The crude oil was then purified by radial chromatography (5-10-20% isopropyl alcohol/hexane, 4 mm plate) to yield 535 mg of [R-(S*,R*)]-α-[1-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl) amino]ethyl]benzenemethanol (90%).

後処理

  1. extractionthe free base extracted with 100 ml ether
  2. dry with materialThe organic was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield an oil which
  6. additionwas added to the stirred reaction
  7. customthe solvent was removed under vacuum
  8. customThe crude oil was then purified by radial chromatography (5-10-20% isopropyl alcohol/hexane, 4 mm plate)

出典と根拠

ORDレコード
ord-b8efe1e099404e899f765374d95c304e
出典データセット
uspto-grants-1995_02
特許番号
US05391739

関連ノート

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