Triethylamine → Benzenepropanol

HRID 973766

Reaction equation

HRID 973766 reaction equation
ClC1N=CN=C2N(C3C=CC=CC=3)N=CC=12.CCN(CC)CC.N[C@H:25]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:26][OH:27]>C(O)C>[C:29]1([CH2:28][CH2:25][CH2:26][OH:27])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2197524-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidineHCID 853475phenylalaninol, (R)-

Product 1

HCID 31234BenzenepropanolYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 1.13 g of the starting material 4-chloro-1-phenylpyrazolo[3,4-d]pyrimidine was combined with 0.67 ml Et3N, 0.74 g of (R)-(+)-2-amino-3-phenyl-1-propanol in 60 ml absolute ethanol and heated in a steam bath for four hours. The solvent was then removed under vacuum and the residue was purified by flash chromatography (10-20% isopropyl alcohol/hexane) to yield 1.24 g of (R)-β-[1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol (74% yield).

Workup

  1. temperatureheated in a steam bath for four hours
  2. customThe solvent was then removed under vacuum
  3. customthe residue was purified by flash chromatography (10-20% isopropyl alcohol/hexane)

Sources & evidence

ORD record
ord-40abb9e613994982a020ae2c4cdf3020
Source dataset
uspto-grants-1991_11
Patent number
US05064947

Linked notes

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