Sodium hydride → 4-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanol

HRID 1487617

Reaktionsgleichung

Reaktionsgleichung von HRID 1487617
[H-].[Na+].[CH3:3][C:4]1([OH:11])[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1.[Cl:12][C:13]1[N:14]=[C:15](Cl)[C:16]2[C:21]([I:22])=[CH:20][N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=2[N:18]=1>C1COCC1>[Cl:12][C:13]1[N:14]=[C:15]([O:10][CH:7]2[CH2:8][CH2:9][C:4]([CH3:3])([OH:11])[CH2:5][CH2:6]2)[C:16]2[C:21]([I:22])=[CH:20][N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]=2[N:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 144496821-Methylcyclohexane-1,4-diolHCID 866796212,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 867264454-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-1-methylcyclohexanolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 1.36 equiv) in dry THF (0.68 M) under nitrogen atmosphere was added 1-methylcyclohexane-1,4-diol (1 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 (0.9 equiv,) in dry THF (0.45 M) was added. The mixture was stirred at room temperature for 2 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 (20 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash column chromatography (0-30% ethyl acetate in petroleum ether) to afford the title compound as a white solid (78% yield). MS (ESI) m/z 538.4 [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 (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel flash column chromatography (0-30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-e32306cdd8734c56a51926d4908d835e
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428509B2

Verknüpfte Notizen

Wird geladen…