Dicyclohexylamine → 6-(Pyrimidin-5-YL)hex-5-YN-1-OL

HRID 982376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982376
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][C:12]#[CH:13].C1(NC2CCCCC2)CCCCC1>[Cu]I.C(#N)C>[N:4]1[CH:3]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:14])[CH:7]=[N:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 7582DicyclohexylamineHCID 702345-Hexyn-1-olHCID 783445-Bromopyrimidine

Produkt 1

HCID 139997526-(Pyrimidin-5-YL)hex-5-YN-1-OLAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5-bromopyrimidine (3.96 g), 5-hexynol (2.44 g), dicyclohexylamine (4 g) and acetonitrile (50 ml) was de-oxygenated by bubbline nitrogen through the solution for 10 min. BTPC (150 mg) and copper (I) iodide (25 mg) were added and the mixture was heated to 60°-70° under nitrogen for 1 h, cooled and evaporated in vacuo. Ether (175 ml) was added, the mixture filtered and evaporated in vacuo and the residue purified by FCC. Elution with ether followed by System C (19:1-92:8) gave the title compound as a pale yellow oil (3.79 g), t.l.c. (System C 17:3) Rf 0.55.

Aufarbeitung

  1. temperaturethe mixture was heated to 60°-70° under nitrogen for 1 h
  2. temperaturecooled
  3. customevaporated in vacuo
  4. additionEther (175 ml) was added
  5. filtrationthe mixture filtered
  6. customevaporated in vacuo
  7. customthe residue purified by FCC
  8. washElution with ether

Quellen und Nachweise

ORD-Eintrag
ord-927f729192e8411fb3c440a2fd8b46e0
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04996218

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