5-Decyloxy-2-(4-bromophenyl)pyrimidine → (-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine

HRID 1956083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956083
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:25][CH:26]([CH3:32])[CH2:27][CH2:28][CH2:29][C:30]#[CH:31]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][CH:26]([OH:25])[CH3:32])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

7

Edukt 2

HCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 133371736-Heptyn-2-ol

Produkt 1

HCID 19437556(-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (25 g), optically active 6-hydroxy-1-heptyne (8.58 g), dichlorobis(triphenylphosphine)palladium (0.1 g), copper iodide (0.1 g), triphenylphosphine (0.52 g) and triethylamine (200 ml) are charged and heated up to 90° C. to carry out a reaction for 10 hours. After evaporating triethylamine off under reduced pressure, toluene and 10% hydrochloric acid are added to the residue for extraction, and the organic layer is washed with water and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]-pyrimidine (23.4 g). [α]D20 =-3.3° (c=1.035, CHCl3).

Aufarbeitung

  1. customIn a reactor equipped with a stirrer
  2. customa reaction for 10 hours
  3. customAfter evaporating triethylamine off under reduced pressure, toluene and 10% hydrochloric acid
  4. additionare added to the residue for extraction
  5. washthe organic layer is washed with water
  6. customevaporated under reduced pressure
  7. customA resulting residue is purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0a96ed2e483e48e98e71a1cefb0b1793
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05779934

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