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Triethylamine → 4-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

HRID 2210632
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2210632
C(N(CC)CC)C.[CH:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl[C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:25]([O:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]2[O:23][CH3:24])[C:17](=[O:47])[N:16]=1>C1COCC1.[Cu]I>[C:8]([C:15]1[CH:20]=[CH:19][N:18]([C@@H:21]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:25]([O:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:22]2[O:23][CH3:24])[C:17](=[O:47])[N:16]=1)#[C:9][CH2:10][CH2:11][CH2:12][CH3:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 217824984-Chloro-1-(2-O-methyl-3,5-di-O-benzoyl-beta-D-ribofuranosyl)-pyrimidin-2-one

Produkt 1

HCID 228567304-(1-Hexyn-1-yl)-1-(2-O-methyl-3,5,-di-O-benzoyl-beta-D-ribofuranosyl)pyrimidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Bis-triphenylphosphine palladium (II) dichloride (422 mg, 4.3 mmole) and copper (I) iodide (114 mg, 4.3 mmole) were suspended in anhydrous THF (100 ml) and degassed with argon for 10 min. The orange suspension was treated with triethylamine (5 ml) and 1-hexyne (2.96 g, 41 mmole) and stirred for 5 min. A solution of 4-chloro-1-(2-O-methyl-3,5,-di-O-benzoyl-β-D-ribofuranosyl)pyrimidin-2-one (6.74 g, 13.9 mmole) in THF (25 ml) was added all at once. The reaction mixture was stirred for 2 hours at room temperature and evaporated to an oil. The residue was purified by silica gel column chromatography. Elution with chloroform (500 ml) and then chloroform/acetone (98:2, 21), pooling of appropriate fractions and evaporation gave a yield of 3.84 g (52.7%).

Aufarbeitung

  1. customdegassed with argon for 10 min
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customevaporated to an oil
  4. customThe residue was purified by silica gel column chromatography
  5. washElution with chloroform (500 ml)
  6. customchloroform/acetone (98:2, 21), pooling of appropriate fractions and evaporation
  7. customgave a yield of 3.84 g (52.7%)

Quellen und Nachweise

ORD-Eintrag
ord-7eb8ab37ea6a48dbbbd5efc937a8fb5b
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05459243

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