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Water → 6-(2-Bromobenzyl)-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 1434542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1434542
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=[O:15].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25](OC)=O.[O-]CC.[Na+].O>C(O)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]1[NH:16][C:14](=[O:15])[C:3]2[CH:4]=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:13])[C:2]=2[N:1]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 119839075-Amino-1-(o-tolyl)-1H-pyrazole-4-carboxamide

Produkt 1

HCID 1354446946-(2-Bromobenzyl)-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.0 g (9.25 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 25A) and 9.5 g (41.62 mmol) of methyl (2-bromophenyl)acetate are dissolved in 30 ml of absolute ethanol under argon, and 3.15 g (46.6 mmol) of sodium ethoxide are added. The reaction mixture is heated to a reflux overnight. Cooling to room temperature is followed by hydrolysis with 50 ml of water and subsequent extraction with ethyl acetate (2×50 ml). The combined organic phases are dried over sodium sulphate, and the solvent is distilled off under reduced pressure. The crude product is then purified by column chromatography (silica gel; mobile phase cyclohexane/ethyl acetate, gradient 10:1→1:1). 3.01 g (82% of theory) of the product are obtained.

Aufarbeitung

  1. temperatureThe reaction mixture is heated to a reflux overnight
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe crude product is then purified by column chromatography (silica gel; mobile phase cyclohexane/ethyl acetate, gradient 10:1→1:1)
  5. custom3.01 g (82% of theory) of the product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-6d29174d13974a62be816ecc8aece48d
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07615558B2

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