Dimethyl malonate → 2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione
Reaktionsgleichung
[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[C:9]=2[CH3:18])=[C:5]([NH2:19])[NH:4][N:3]=1.[C:20](OC)(=[O:26])[CH2:21][C:22](OC)=[O:23].C[O-].[Na+]>CO>[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:17])[F:16])[C:9]=2[CH3:18])=[C:5]2[NH:19][C:20](=[O:26])[CH2:21][C:22](=[O:23])[N:4]2[N:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 3-methyl-4-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-5-amine (2.0 g, 7.43 mmol), dimethyl propanedioate (1.03 g, 7.8 mmol) and in methanol (20 mL) stirred under nitrogen at 20° C. was added a solution of sodium methoxide (3.21 g, 14.9 mmol) in methanol (20 mL) dropwise during 15 minutes. The reaction mixture was stirred at 80° C. for overnight. After the reaction mixture was cooled to room temperature, precipitate was collected by filtration, then washed with methanol (5 mL×2). Product was dried under air. The product was then suspended with 1 N HCl (10 mL), stirred for 10 minutes, and filtered off HCl solution. The product was dried and used in next step without further purification. (2.41 g, 96%); LC/MS: MS (ES+) m/e 338 (MH+).
Aufarbeitung
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationprecipitate was collected by filtration
- washwashed with methanol (5 mL×2)
- customProduct was dried under air
- stirringstirred for 10 minutes
- filtrationfiltered off HCl solution
- customThe product was dried
- customused in next step without further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-f1942086662845e69fa6b0d0efb332fc
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09096605B2
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