Potassium Carbonate → HCID 178480367, Verbindung

HRID 630186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630186
[SH:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[C:25]([Cl:26])=[CH:24][N:23]([CH3:27])[N:22]=1>CN(C=O)C>[Cl:26][C:25]1[C:21]([CH2:20][S:1][C:2]2[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[N:3]=2)=[N:22][N:23]([CH3:27])[CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 595893993-(bromomethyl)-4-chloro-1-methyl-1H-pyrazoleHCID 178516148HCID 178516148, Verbindung

Produkt 1

HCID 178480367HCID 178480367, VerbindungAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (721 mg, 3.7 mmol) was dissolved in anhydrous DMF (20 mL), and then potassium carbonate (1.53 g, 11.0 mmol) and 3-(bromomethyl)-4-chloro-1-methyl-1H-pyrazole (4.7 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, and the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 4-10% DCM/MeOH to afford 2-{[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (135 mg, 11% yield for 2 steps); 1H NMR (400 MHz, DMSO-d6): δ 3.78 (s, 3H), 4.39 (s, 2H), 6.66 (s, 1H), 7.93 (s, 1H).

Aufarbeitung

  1. customThe solid was removed by filtration
  2. washwashed with methanol
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 4-10% DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-a236dba2a55442fe947b5385c74b415c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315521B2

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