Lithium iodide → (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine
Reaktionsgleichung
[I-:1].[Li+].CS(O[CH2:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@H:16]2[CH3:21])[N:12]=[C:11]([Cl:22])[N:10]=1)(=O)=O>O1CCOCC1>[Cl:22][C:11]1[N:12]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@H:16]2[CH3:21])[CH:14]=[C:9]([CH2:8][I:1])[N:10]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Lithium iodide (17.57 g, 131.27 mmol) was added to (R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate (19.2 g, 59.67 mmol) in dioxane (300 ml) and heated to 100° C. for 2 hours under nitrogen. The reaction mixture was quenched with water (200 ml) and extracted with EtOAc (3×200 ml). The organic layers were combined and washed with 2M sodium bisulfite solution (400 ml), water (400 ml), brine (400 ml) dried over MgSO4 and then evaporated. The residue was triturated with Et2O to afford (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine (13.89 g, 66%); 1H NMR (400 MHz, CDCl3) 1.32 (3H, d), 3.28 (1H, td), 3.54 (1H, td), 3.69 (1H, dd), 3.78 (1H, d), 3.98-4.02 (2H, m), 4.21 (2H, s), 4.29 (1H, br s), 6.41 (1H, s); m/z: (ESI+) MH+, 354.31.
Aufarbeitung
- customThe reaction mixture was quenched with water (200 ml)
- extractionextracted with EtOAc (3×200 ml)
- washwashed with 2M sodium bisulfite solution (400 ml), water (400 ml), brine (400 ml)
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was triturated with Et2O
Quellen und Nachweise
- ORD-Eintrag
- ord-779c2140ade7478b86ddcae4ce713995
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US08999997B2
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