Propargyl alcohol → HCID 22599874, Verbindung

HRID 1759802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1759802
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].Cl[C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=[CH:10][N:9]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:15]([O:14][C:12]1[CH:13]=[C:8]([O:6][CH2:3][C:4]#[CH:5])[N:9]=[CH:10][N:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225998714-(Benzyloxy)-6-chloropyrimidine

Produkt 1

HCID 22599874HCID 22599874, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

In 4 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 0.7 ml of a tetrahydrofuran solution containing 0.12 g of 2-propyn-1-ol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes and then cooled to 0° C., to which 0.7 ml of a tetrahydrofuran solution containing 0.4 g of 4-chloro-6-benzyloxypyrimidine was slowly added dropwise. The mixture was further stirred at 0° C. for 4.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.17 g of 4-benzyloxy-6-(2-propynyloxy)pyrimidine (the present compound (13)).

Aufarbeitung

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringThe mixture was further stirred at 0° C. for 4.5 hours
  5. extractionextracted three times with chloroform
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b115c489177644c7b24e4621521d5fe4
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838463B2

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