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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
Notes
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Reaction equation

HRID 275009 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-b8efe1e099404e899f765374d95c304e
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05391739

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes