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Acetic Acid → 2-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

HRID 19666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19666
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH3:19])[N:13]=1.C(O)(=O)C>O1CCOCC1.O>[CH3:19][S:18][C:14]1[N:15]=[C:16]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:12][N:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidine

Produkt 1

HCID 111838682-(Methylthio)-4-[(phenylmethyl)oxy]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Benzyl alcohol (1.3 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil, 0.74 g) in 12.4 mL of dry dioxane, and the mixture was stirred at 100° C. for 30 min. A solution of 4-chloro-2-(methylthio)pyrimidine (2.0 g) in dry dioxane (8.2 mL) was added dropwise at 50° C. and the mixture was stirred at this temperature for 5 hours. After cooling at room temperature the mixture was acidified with glacial acetic acid, treated with water and extracted with dichloromethane. The organic phases were dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (70 g) eluting with ciclohexane/ethyl acetate from 95/5 to 9/1 to give the title compound as a white solid (1.22 g).

Aufarbeitung

  1. stirringthe mixture was stirred at this temperature for 5 hours
  2. temperatureAfter cooling at room temperature the mixture
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by a silica SPE cartridge (70 g)
  8. washeluting with ciclohexane/ethyl acetate from 95/5 to 9/1

Quellen und Nachweise

ORD-Eintrag
ord-cf272e86264b42c7abe6ebbb6c17ca0d
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07745458B2

Notizen zur Reaktion

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