Sodium hydride → HCID 58056314, Verbindung

HRID 1773567

Reaktionsgleichung

[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][NH:11][C:12]=1[NH2:13])=[O:7])[CH3:4].[O:14]1[CH2:19][CH2:18][CH2:17][C:16]([CH:20]=O)=[CH:15]1>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:20]=[C:16]([CH2:17][CH2:18][CH2:19][OH:14])[CH:15]=[N:13][C:12]=12)=[O:7])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Sodium hydride (60% suspension in mineral oil, 350 mg, 8.78 mmol) was added, at 0° C., to a solution of 5-amino-1H-pyrazole-4-carboxylic acid ethyl ester (1.4 g, 8.9 mmol) and 5,6-dihydro-4H-pyran-3-carbaldehyde (0.5 g, 4.5 mmol) in anhydrous N,N-dimethylformamide (10 mL) and the resulting mixture was stirred, at 0° C., for 30 minutes. The reaction mixture was stirred at room temperature overnight and then heated at 50° C. for 2 hours. The resulting mixture was partitioned between water and ethyl acetate and the organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography to afford 0.24 g of 6-(3-hydroxy-propyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester as a white solid. MS=250 [M+H]+.

Aufarbeitung

stirringThe reaction mixture was stirred at room temperature overnight
temperatureheated at 50° C. for 2 hours
customThe resulting mixture was partitioned between water and ethyl acetate
customthe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-822402bd765b44ba96d520e40ab69b06
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09255110B2

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