Isopropanol → HCID 86726464, Verbindung

HRID 1487636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487636
[H-].[Na+].[CH3:3][CH:4]([OH:6])[CH3:5].[Cl:7][C:8]1[N:9]=[C:10](Cl)[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1>C1COCC1>[Cl:7][C:8]1[N:9]=[C:10]([O:6][CH:4]([CH3:5])[CH3:3])[C:11]2[C:16]([I:17])=[CH:15][N:14]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=2[N:13]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 866796212,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 86726464HCID 86726464, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (1 equiv, 60% in mineral oil) in dry THF (0.9 M) under nitrogen atmosphere was added propan-2-ol (0.52 equiv). The reaction mixture was stirred at room temperature for 30 min before a solution of 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (0.5 equiv) in dry THF (0.45 M) was added. The mixture was stirred at room temperature for 1 h. The reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether) to afford the title compound as a yellow oil (81% yield). MS (ESI) m/z 468.2 [M+1]+.

Aufarbeitung

  1. additionwas added
  2. customUpon completion, the reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel flash column chromatography (0-10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-dc763d57bd204e3aa72314eb90a51d62
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428509B2

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