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HCID 11197766, Verbindung → HCID 67355138, Verbindung

HRID 1846143
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1846143
[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]CCCC.Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1.CCCCC>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH3:23])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:12]([CH2:14][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11197766HCID 11197766, VerbindungHCID 67353995HCID 67353995, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 67355138HCID 67355138, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution at −78° C. containing 500 mg (1.62 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyrimidine (6) in 10 mL of anhydrous THF were added 1.11 mL (1.76 mmol) of a 1.6 M solution of n-BuLi in pentane followed by 509 mg (1.62 mmol) of 9-bromo-1-(benzyloxy)nonane (1). The reaction mixture was stirred under argon atmosphere at −78° C. for 30 min. then the reaction mixture was warmed to room temperature slowly, and the reaction mixture was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and the poured into 70 mL of water. The mixture was then extracted with two portions of 70 mL of ethyl acetate. The combined organic solution was then washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 5:1 gave the expected product as light yellow oil: yield 175 mg (20%). 1H-NMR (CDCl3) δ 7.48-7.37 (m, 10H), 5.93 (s, 2H), 4.94 (s, 2H), 4.55 (s, 2H), 3.51 (t, 2H, J=6.8), 2.84 (t, 2H, J=7.6) 2.52 (s, 3H), 2.39 (s, 6H), 1.82 (m, 2H), 1.65 (m, 2H), 1.33 (m, 12H); 13C-NMR (CDCl3) δ 165.16, 161.60, 152.48, 147.71, 138.79, 136.28, 129.16, 128.59, 128.26, 107.99, 75.29, 72.96, 70.70, 31.70, 29.85, 29.62, 29.52, 27.79, 26.27, 22.73, 19.32, 14.37

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to room temperature slowly
  2. stirringthe reaction mixture was stirred overnight
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. additionthe poured into 70 mL of water
  5. extractionThe mixture was then extracted with two portions of 70 mL of ethyl acetate
  6. washThe combined organic solution was then washed with a portion of 100 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under diminished pressure
  9. customThe residue was purified by chromatography on a silica gel column
  10. washElution with hexanes-ethyl acetate 5:1

Quellen und Nachweise

ORD-Eintrag
ord-0f90948421584e88bbabaa450cea1539
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952025B2

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