Reaktion #169291

Reaktionsgleichung

Water

Potassium carbonate

2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide

2-(4-Chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide

chloromethyl methyl sulfide

→

title compound

Ausbeute 36.0%

2-(4-chlorophenyl)-N-[5-({7-[(methylthio)methyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}carbonyl)pyridin-3-yl]acetamide

Ausbeute 36.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with EtOAc (3×5 mL)
2. 2
   WaschenThe combined organic fractions were washed with water (5 mL), brine (5 mL)
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigeto give a pale yellow oil
6. 6
   SonstigeThe crude material was purified by column chromatography on silica gel (gradient of 100% DCM to 90:10:1 DCM/MeOH/NH3)

Vorschrift

Potassium carbonate (38 mg, 0.275 mmol) was added to a stirring solution of 2-(4-chlorophenyl)-N-[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylcarbonyl)pyridin-3-yl]acetamide (Example 308, 60.0 mg, 0.153 mmol) in DMF (1.0 mL) at room temperature. After 10 min, chloromethyl methyl sulfide (19 μL, 0.23 mmol) was added to the mixture and the reaction was stirred for 24 hours at room temperature. Water (3 mL) was added to the mixture and it was extracted with EtOAc (3×5 mL). The combined organic fractions were washed with water (5 mL), brine (5 mL), dried over magnesium sulfate and concentrated under reduced pressure to give a pale yellow oil. The crude material was purified by column chromatography on silica gel (gradient of 100% DCM to 90:10:1 DCM/MeOH/NH3) to give the title compound as a pale yellow solid in 36% yield, 25 mg.

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