Chloromethyl Methyl Ether → 4-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1847051
C(N(CC)C(C)C)(C)C.Cl[CH2:11][O:12][CH3:13].[Si:14]([O:21][CH2:22][CH:23]([OH:38])[CH2:24][N:25]1[C:30](=[O:31])[CH:29]=[N:28][C:27]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[N:35][C:26]1=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>ClCCl>[Si:14]([O:21][CH2:22][CH:23]([O:38][CH2:11][O:12][CH3:13])[CH2:24][N:25]1[C:30](=[O:31])[CH:29]=[N:28][C:27]2[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[N:35][C:26]1=2)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 867249764-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Produkt 1

HCID 867249774-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

N,N-Diisopropylethylamine (1.93 ml, 11.10 mmol) and chloromethylmethyl ether (0.56 ml, 7.40 mmol) were added under cooling on ice to a solution of 4-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.35 g, 3.70 mmol) in dichloromethane (20 ml) and the mixture was stirred for 24 hours. The reaction solution was diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1.02 g (67%) of the title compound in the form of a yellow oily product.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-79cc8392f1d741b2a80ea68bb89dc631
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952010B2

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