phenylalaninol, (R)- → HCID 15667126, compound

HRID 1728918Notes

Reaction equation

HRID 1728918 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 853475phenylalaninol, (R)-HCID 47371094,6-dichloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 15667126HCID 15667126, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 2.81 g of 1-phenyl-4,6-dichloropyrazolo[3,4-d]pyrimidine was suspended in 60 ml of ethanol, then 3.2 g of (R)-(+)-2-amino-3-phenyl-1-propanol was added with stirring. After 48 hours the solvent was removed under vacuum and the oil was flash chromatographed (2-5-7% MeOH/CHCl3) to yield 3.80 g of (R)-β-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol (95%). Next, 380 mg of sodium was reacted with 10 ml of n-propanol. 773 mg of (R)-β-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol in 5 ml of n-propanol was added with stirring. The reaction was heated to 90° C. in an oil bath for 2.5 hours, then the solvent was removed under vacuum, the residue taken up in 200 ml CHCl3. The organic layer was washed with saturated NaCl, dried over MgSO4, filtered, and concentrated to an oil which was purified by radial chromatography (10-20-30% isopropyl alcohol/hexane, 4 mm plate) to yield after recrystallization from 30% isopropyl alcohol/hexane 217 mg of a white solid (m.p. 158°-159° C.). Proton NMR indicated n-propanol was still present, so this product was oven dried under vacuum (setting at 3) to yield 161 mg of final product, (R)-β-[(1-phenyl-6-propoxy-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amino]benzenepropanol (m.p. 157°-158° C.).

Workup

  1. customAfter 48 hours the solvent was removed under vacuum
  2. customchromatographed (2-5-7% MeOH/CHCl3)

Sources & evidence

ORD record
ord-07197c51e6e44c47b747d37860cdcc83
Source dataset
uspto-grants-1994_07
Patent number
US05329007

Reaction notes

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