Dimethylformamide → 6-Chloro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine

HRID 2240263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240263
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12)[NH2:5].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[N:23]=[C:22](N)[N:21]=1.[OH-].[Na+].C[N:31](C=O)C>O.Cl>[Cl:19][C:20]1[N:21]=[C:22]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([CH2:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[NH:16][CH:17]=[CH:18][C:11]=34)=[C:2]([F:1])[CH:3]=2)[N:23]=[C:24]([NH2:31])[CH:25]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidineHCID 593050333-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

Produkt 1

HCID 866243416-Chloro-N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

40 mg (0.15 mmol) of 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline and 29 mg (0.18 mmol) of 4,6-dichloropyrimidine-2-amine are suspended in 2 ml of water and 0.11 ml of 2N hydrochloric acid. The reaction mixture is heated at reflux for 15 hours. After cooling, the mixture is made alkaline using dilute aqueous sodium hydroxide solution, a little DMF is added and the mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 15 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe extract is dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5ede3aec739b472c823b971a2d21b95e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723347B2

Notizen zur Reaktion

Wird geladen…