Chlorosuccinimide → 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 29886

Reaktionsgleichung

Reaktionsgleichung von HRID 29886
[Cl:1][C:2]1[C:3]2[C:10](C)=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12]N1C(=O)CCC1=O>ClCCl>[Cl:1][C:2]1[C:3]2[C:10]([Cl:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidine

Produkt 1

HCID 111060924,5-dichloro-7H-pyrrolo[2,3-d]pyrimidineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
43 °C

Versuchsvorschrift

Following the procedure in Pdulo, J. S.; Saxena, N. K.; Nassiri, M. R.; Turk, S. R.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 31:2086 (1988), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (Example 1A, 20. g, 0.13 mol) was suspended in anhydrous dichloromethane (500 mL), followed by addition of N-chlorosuccinimide (20.8 g, 0.160 mol). The reaction mixture was refluxed at 43° C. for 8 hours. The reaction was cooled down, and the white solid was filtered, washed with dichloromethane (300 mL), and dried to give 4,5-dichloro-7H-pyrrolo[2,3-d]pyrimidine (20 g, 83%)

Aufarbeitung

  1. temperatureThe reaction was cooled down
  2. filtrationthe white solid was filtered
  3. washwashed with dichloromethane (300 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-924c8fe2692a4db982491774cdedb9b6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423043B2

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