Sodium hydride → 4-Chloro-6-{1-[2-(3,5-dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine

HRID 1620843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620843
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][C:11]1[CH:15]=[C:14]([CH3:16])[N:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]([OH:28])[C:24]([F:27])([F:26])[F:25])[N:12]=1.[H-].[Na+]>C1COCC1>[Cl:8][C:6]1[CH:5]=[C:4]([O:28][CH:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:13]2[C:14]([CH3:16])=[CH:15][C:11]([CH3:10])=[N:12]2)[C:24]([F:25])([F:27])[F:26])[N:3]=[C:2]([NH2:1])[N:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 667426631-[2-(3,5-Dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethanol

Produkt 1

HCID 866210944-Chloro-6-{1-[2-(3,5-dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamineAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
42.5 °C

Versuchsvorschrift

2-Amino-4,6-dichloro pyrimidine (0.074 g, 0.45 mmol), 1-[2-(3,5-dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethanol (0.120 g, 0.45 mmol), NaH (0.022 g, 0.59 mmol) were added to anhydrous THF (10 ml) under nitrogen atmosphere. The reaction was stirred at 40-45° C. for 6 h, and then cooled to room temperature, and quenched with water (0.2 ml). The reaction mixture was concentrated to give crude 4-chloro-6-{1-[2-(3,5-dimethyl-pyrazol-1-yl)-phenyl]-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine (0.195 g, >90% pure by LCMS) which was directly used in the following step.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with water (0.2 ml)
  3. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-46da8df6a13e40fdb2586c36ce4e4861
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772482B2

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