Methanesulfinic acid → 2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine
Reaktionsgleichung
[CH3:1][S:2]([OH:4])=[O:3].[Na].[Cl:6][C:7]1[N:12]=[C:11]([CH2:13]I)[CH:10]=[C:9]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[N:8]=1>C(#N)C>[Cl:6][C:7]1[N:8]=[C:9]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[CH:10]=[C:11]([CH2:13][S:2]([CH3:1])(=[O:4])=[O:3])[N:12]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
Methanesulfinic acid, sodium salt (11.75 g, 115.11 mmol) was added in one portion to 2-chloro-4-(iodomethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (37 g, 104.64 mmol), in acetonitrile (900 mL) and the resulting solution stirred at 85° C. for 24 hours. The organic layers were combined and washed with water (3×100 mL), dried over MgSO4, filtered, and the solvent was removed by evaporation to give the crude product as a dark brown oil, which solidifed (36 g). The crude solid was purified by flash silicachromatography, elution gradient 0 to 30% ethyl acetate in DCM, to give the desired material (22 g) as a cream solid which was identical to previous samples.
Aufarbeitung
- washwashed with water (3×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent was removed by evaporation
- customto give the crude product as a dark brown oil, which
- customThe crude solid was purified by flash silicachromatography, elution gradient 0 to 30% ethyl acetate in DCM
Quellen und Nachweise
- ORD-Eintrag
- ord-9732cb5bbd2b4ddeaffd58c58ffe9b35
- Quelldatensatz
- uspto-grants-2012_03
- Patentnummer
- US08138183B2
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