Iodine → 2-Chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine
Reaktionsgleichung
[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[O:10][CH:9]=[CH: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[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][C:9]([I:22])=[CH:8][C:6]=2[N:7]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (50 mg, 1.0 eq) dissolved in THF (2.1 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.17 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. A solution of iodine (159 mg, 3.0 eq) in THF (0.6 ml) 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 2-chloro-6-iodo-4-morpholinofuro[3,2-d]pyrimidine 45 (63 mg, 83%): MS (Q1) 366 (M)+.
Aufarbeitung
- customReaction mixture
- customreaction mixture
- temperatureto slowly warm up to room temperature
- stirringstirred for 45 minutes
- customThe reaction mixture was quenched with saturated aq. Na2S2O3
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated
- customThe crude reaction mixture
- customwas purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-4dfb397b5fc349f5b7ae70e7959a5b5c
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08993563B2
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