Sodium Iodide → 2-chloro-6-methyl-N-(1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 383799

Reaktionsgleichung

Reaktionsgleichung von HRID 383799
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[C:14]([NH2:15])=[CH:13][CH:12]=[N:11]1.[Na+].[I-].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:14]2[NH:10][N:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 74561Pyrazol-3-ylamineHCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531Diisopropylethylamine

Produkt 1

HCID 580550402-chloro-6-methyl-N-(1H-pyrazol-3-yl)pyrimidin-4-amineAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the solution of 2,4-dichloro-6-methylpyrimidine (3.00 g) and 1H-pyrazol-5-amine (1.31 g) in NMP (30 ml) was added NaI (2.36 g) and DIEA (6.33 ml). And the mixture was heated to 80° C. under stirring. After 1 day, the mixture was cooled to room temperature. The mixture was diluted with EtOAc. The precipitate was collected by filtration, washed with the mixed solvent of hexane and EtOAc and dried in vacuo to give 2-chloro-6-methyl-N-(1H-pyrazol-5-yl)pyrimidin-4-amine (2.60 g) as a pale pink solid.

Aufarbeitung

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with the mixed solvent of hexane and EtOAc
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-463b30d362164ec98a3e5b14858f956d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367690B2

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