Methanol → HCID 178418674, Verbindung

HRID 2226013

Reaktionsgleichung

Reaktionsgleichung von HRID 2226013
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[N:20]=[C:14]2[N:13]=[CH:12]1.CO.N1C2C(=CC=CC=2)C=CC=1.[H][H]>[Pd].CCOCC.C(Cl)(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[CH:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:24])[CH3:26])[N:20]=[C:14]2[N:13]=[CH:12]1

Komponenten

8

Edukt 4

HCID 887MethanolHCID 7047QuinolineHCID 178418361HCID 178418361, VerbindungHCID 178418609HCID 178418609, Verbindung

Produkt 1

HCID 178418674HCID 178418674, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 2 g of 3-(3-tetrahydropyr-2-yloxyprop-1-yn-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 40 ml of methanol, 20 ml of chloroform, 40 mg of 5% palladium on barium sulfate, and 40 mg of synthetic quinoline is stirred under 1 atmosphere hydrogen pressure for 40 min. The solvent then is removed by evaporation and the residue diluted with methylene chloride. The methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride to remove catalyst and the filtrate then concentrated to give an oil which upon adding ether yields 3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which can be further purified through column chromatography eluting with ethyl acetate and recrystallization using ethyl acetate.

Aufarbeitung

  1. customThe solvent then is removed by evaporation
  2. additionthe residue diluted with methylene chloride
  3. filtrationThe methylene chloride solution is filtered through silica gel with 2% methanol in methylene chloride
  4. customto remove catalyst
  5. concentrationthe filtrate then concentrated
  6. customto give an oil which

Quellen und Nachweise

ORD-Eintrag
ord-9eb22346ec214f20a418d9f2245ec66a
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344932

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