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Dichloromethane → 5-Iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidine

HRID 2387748
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2387748
C(N(CC)C(C)C)(C)C.ClCCl.[I:13][C:14]1[C:15]([OH:22])=[N:16][C:17]([CH3:21])=[N:18][C:19]=1[CH3:20].[CH3:23][O:24][CH2:25]Cl>O>[I:13][C:14]1[C:15](=[O:22])[N:16]([CH2:23][O:24][CH3:25])[C:17]([CH3:21])=[N:18][C:19]=1[CH3:20].[I:13][C:14]1[C:15]([O:22][CH2:23][O:24][CH3:25])=[N:16][C:17]([CH3:21])=[N:18][C:19]=1[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 178432770HCID 178432770, Verbindung

Produkt 2

HCID 672831815-Iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidineHCID 674740695-iodo-3-(methoxymethyl)-2,6-dimethylpyrimidin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

N,N-diisopropylethylamine (13.1 ml) was added to a dichloromethane (100 ml) solution of the compound 326-2 (14.5 g). Chloromethyl methyl ether (4.85 ml) was added to the reaction solution, while the solution was stirred at −40° C. The obtained mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 0:1), so as to obtain the title compound (10.6 g) and 5-iodo-4-(methoxymethoxy)-2,6-dimethylpyrimidine (2.55 g).

Aufarbeitung

  1. stirringThe obtained mixture was stirred at room temperature for 15 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=19:1 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-6596d1464a1c458f808f6a3bc5bba5f9
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08268848B2

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