Ammonia → 3-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

HRID 570554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570554
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]([C:21]([CH3:27])([CH3:26])[C:22](OC)=[O:23])=[C:18](O)[N:19]=2)=[N:6]1.P(Cl)(Cl)(Cl)=O.[NH3:37]>C(#N)C>[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[N:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]3[C:21]([CH3:26])([CH3:27])[C:22](=[O:23])[NH:37][C:18]=3[N:19]=2)=[N:6]1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500128HCID 178500128, Verbindung

Produkt 1

HCID 717468173-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-7,7-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

186 mg (0.438 mmol) of methyl 2-{3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}-2-methylpropanoate were admixed with 4 ml (42.913 mmol) of phosphoryl chloride and the mixture was stirred at RT for 2.5 h. The reaction solution was diluted with 20 ml of dry acetonitrile and gradually added dropwise while cooling with ice to 30 ml of a 25% aqueous ammonia solution, and the mixture was stirred at RT overnight. The reaction mixture was concentrated on a rotary evaporator and the precipitate was filtered off. 127 mg of the target compound were obtained (74% of theory).

Aufarbeitung

  1. additiongradually added dropwise
  2. stirringthe mixture was stirred at RT overnight
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. filtrationthe precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-dc704b87509d4fbf97f8101743c765a0
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023849B2

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