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

反应方程式

HRID 275009 反应方程式
[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

参与物

6

反应物 3

HCID 90652-Amino-1-phenylpropan-1-ol hydrochlorideHCID 14797氢氧化钾HCID 47371094,6-二氯-1-苯基-1氢-吡唑[3,4-D]并嘧啶

产物 1

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

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

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%).

后处理

  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)

来源与证据

ORD记录
ord-b8efe1e099404e899f765374d95c304e
来源数据集
uspto-grants-1995_02
专利号
US05391739

关联笔记

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