Acetonitrile → 3-((7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

HRID 624743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624743
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[CH:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.C(N(CC)CC)C.C(#N)C>O>[CH:20]1([NH:23][C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([CH2:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])[CH:3]=2)[CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 866546533-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

Produkt 1

HCID 672169163-((7-(Cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrileAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the reaction flask, 3-((7-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (400 mg, 1.5 mmol) was added along with cyclopropylamine (115 μL, 1.6 mmol), triethylamine (230 μL, 1.6 mmol), and acetonitrile (3 mL). The reaction was stirred at room temperature for 8 hours at 80° C. then cooled to room temperature, diluted with water, filtered and washed with water. The product, 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 83% yield after drying under vacuum overnight. LCMS (M+1=290)

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water
  4. customThe product, 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 83% yield
  5. customafter drying under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-0674d9149cfc4da292533af68e9d9638
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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