phenylalaninol, (S)- → (S)-beta-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol

HRID 973767

Reaction equation

HRID 973767 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.[NH2:18][C@@H:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][OH:21]>C(O)C>[C:1]1([N:7]2[C:11]3=[N:12][C:13]([Cl:17])=[N:14][C:15]([NH:18][C@@H:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][OH:21])=[C:10]3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 47371094,6-dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 15667125(S)-beta-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanolYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of the starting material 1-phenyl-4,6-dichloropyrazolo[3,4-d]pyrimidine was suspended in 60 ml of ethanol. Next, 4.28 g of (S)-(-)-2-amino-3-phenyl-1-propanol was added and the reaction was allowed to stir for 24 hours. The solvent was then removed under vacuum and the crude oil was purified by flash chromatography (10-15-20% isopropyl alcohol/hexane) to yield 3.5 g of (S)-β-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol (97%).

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe crude oil was purified by flash chromatography (10-15-20% isopropyl alcohol/hexane)

Sources & evidence

ORD record
ord-86082389e41941b6925f0e2b852e457e
Source dataset
uspto-grants-1991_11
Patent number
US05064947

Linked notes

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