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Ammonia → 3-[1-(2-Fluorobenzyl)-6-methyl-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 570551
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 570551
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[N:17][C:18]([C:22]([CH3:28])([CH3:27])[C:23](OC)=[O:24])=[C:19](O)[N:20]=2)=[N:6]1.P(Cl)(Cl)(Cl)=O.[NH3:38]>C(#N)C>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[N:17][C:18]3[C:22]([CH3:27])([CH3:28])[C:23](=[O:24])[NH:38][C:19]=3[N:20]=2)=[N:6]1
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Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178500127HCID 178500127, Verbindung

Produkt 1

HCID 717466383-[1-(2-Fluorobenzyl)-6-methyl-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

182 mg (0.42 mmol) of methyl 2-{3-[1-(2-fluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-hydroxy-1,2,4-triazin-6-yl}-2-methylpropanoate were admixed with 3.8 ml (40.87 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 40 ml of a 25% aqueous ammonia solution, and the mixture was stirred at RT for 2 h. The reaction mixture was concentrated on a rotary evaporator and the precipitate was filtered off. The residue was stirred with DMF/methanol and filtered with suction, and the solids were dried under high vacuum. 98 mg of the target compound were obtained (purity 92%; 53% of theory).

Aufarbeitung

  1. additiongradually added dropwise
  2. stirringthe mixture was stirred at RT for 2 h
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator
  4. filtrationthe precipitate was filtered off
  5. stirringThe residue was stirred with DMF/methanol
  6. filtrationfiltered with suction
  7. customthe solids were dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-89e2e6fd060f44aa8596067556f3c0d4
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09023849B2

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