Acetone → 2-(5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol
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[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.C([N-]C(C)C)(C)C.[Li+].[CH3:25][C:26]([CH3:28])=[O:27].C(Cl)Cl>O1CCCC1.CCCCCCC.O1CCCC1.C(C1C=CC=CC=1)C>[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]([C:26]([OH:27])([CH3:28])[CH3:25])[S:8][C:6]=2[N:7]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
4-(5-Chlorothiazolo[5,4-d]pyrimidin-7-yl)morpholine 14 was slurried in tetrahydrofuran and cooled to −78° C. under nitrogen. Two equivalents of 2M lithium diisopropylamide in heptane/tetrahydrofuran/ethylbenzene was added slowly and the solution was stirred for 30 minutes. Acetone (6 eq) was added and the solution was stirred at −78° C. for an additional one hour. Ice was added and the solution was warmed to room temperature before extraction with methylene chloride. The organic layer was dried with sodium sulfate and concentrated. The resulting residue was purified on silica gel to give the light yellow solid of 2-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)propan-2-ol 68.
Aufarbeitung
- stirringthe solution was stirred at −78° C. for an additional one hour
- additionIce was added
- dry with materialThe organic layer was dried with sodium sulfate
- concentrationconcentrated
- customThe resulting residue was purified on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-c8e6be6f7d9046dab2b7d67bdee17cd4
- Quelldatensatz
- uspto-grants-2011_02
- Patentnummer
- US07893059B2
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