4-Toluenesulfonyl chloride → 2,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

HRID 2046992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046992
[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][NH:8][C:6]=2[N:7]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:12])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 529828092,4-Dichloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 582908522,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

503 mg 2,4-dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (5) (2.5 mmol) and 523 mg TsCl (2.75 mmol) were dissolved in 20 mL of DMF. After cooling to 0° C., 200 mg NaH (2.75 mmol) was slowly added under N2. The reaction mixture was stirred at 0° C. for 30 minutes and quenched by adding 10 mL of 10% aqueous NH4Cl at this temperature, then extracted with EtOAc (3×50 mL). Combined organic layers were washed with brine, dried over Na2SO4 and purified by flash column chromatography to give the title compound as light yellow solid.

Aufarbeitung

  1. customquenched
  2. additionby adding 10 mL of 10% aqueous NH4Cl at this temperature
  3. extractionextracted with EtOAc (3×50 mL)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f644aa95376942b6b6f3e4852a135056
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592432B2

Notizen zur Reaktion

Wird geladen…