Reaktion #561179

Reaktionsgleichung

6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine

2-methylquinoline-6-thiol

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product

Ausbeute 19.1%

2-(2-methylquinolin-6-ylthio)-6-chloro-N-(3-methyl-1H-pyrazol-5-yl)pyrimidin-4-amine

Ausbeute 19.1%

Lösungsmittel

ethyl acetate

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   FiltrationThe mixture was filtered
3. 3
   Sonstigeto remove unreacted
4. 4
   Sonstigethe organic layer removed form the filtrate
5. 5
   ExtraktionThe aqueous layer was extracted with ethyl acetate
6. 6
   Waschenthe combined organic extracts washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe crude was purified on silica gel
11. 11
    Wascheneluting with 90 to 100% ethyl acetate/petrol
12. 12
    SonstigeThe title compound was further purified by trituration with dichloromethane

Vorschrift

To a stirred suspension of 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (2.02 g, 7.03 mmol) in tert-butanol (20 ml) was added 2-methylquinoline-6-thiol (1.23 g, 7.03 mmol). The mixture was heated to 70° C. for 4 hours, then cooled to ambient and diluted with ethyl acetate/saturated aqueous potassium carbonate. The mixture was filtered to remove unreacted starting material and the organic layer removed form the filtrate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts washed with brine, dried (MgSO4), filtered and concentrated. The crude was purified on silica gel, eluting with 90 to 100% ethyl acetate/petrol. The title compound was further purified by trituration with dichloromethane. This gave the product as a white solid (514 mg, 19%); MS ES+383.25, ES−381.36.

Quelle