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

HRID 1886010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886010
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>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

5

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 1

HCID 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 bubbling 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. customby bubbling nitrogen through the solution for 10 min
  2. additionBTPC (150 mg) and copper (I) iodide (25 mg) were added
  3. temperaturethe mixture was heated to 60°-70° under nitrogen for 1 h
  4. temperaturecooled
  5. customevaporated in vacuo
  6. additionEther (175 ml) was added
  7. filtrationthe mixture filtered
  8. customevaporated in vacuo
  9. customthe residue purified by FCC
  10. washElution with ether

Quellen und Nachweise

ORD-Eintrag
ord-a6dcb8a042614ccfb934c4ee5fed4e2f
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149698

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