Iodine → 4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

HRID 1365781

Reaktionsgleichung

Reaktionsgleichung von HRID 1365781
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([Li])CCC.[I:22]I>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:5]2[N:10]=[C:9]([I:22])[S:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 576853854-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholineHCID 178418339Butyllithium

Produkt 1

HCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4-(5-chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 dissolved in THF at −78° C. was added 1.6M solution of n-butyllithium in hexanes). The reaction mixture was stirred at −78° C. for 30 minutes. A solution of iodine in THF was added and reaction mixture was allowed to slowly warm up to room temperature and stirred for 45 minutes. The reaction mixture was quenched with saturated aq. Na2S2O3, and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated. The crude reaction mixture was purified by flash chromatography to yield 4-(5-chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18.

Aufarbeitung

  1. customreaction mixture
  2. temperatureto slowly warm up to room temperature
  3. stirringstirred for 45 minutes
  4. customThe reaction mixture was quenched with saturated aq. Na2S2O3
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude reaction mixture
  9. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9d4b888d482e4e0bab634316bb35d1ed
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893059B2

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