Dimethylformamide → 3-((7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile
Reaktionsgleichung
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][CH:13]=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.CN([CH:31]=[O:32])C>>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:31]=[O:32])=[C:9]3[N:8]=[C:7]([CH2:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:6]=2)[CH2:3][CH2:2]1Komponenten
4
Versuchsvorschrift
To 3-((7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile (69 mg, 0.24 mmol) in DMF (0.6 mL), POCl3 (130 μL, 1.4 mmol) was added at room temperature. After the addition was complete, the reaction was stirred for 1 hour at room temperature. Then, the reaction was quenched by addition to ice cold 6N NaOH. The mixture was diluted with water and the solid was collected by filtration. The solid was washed several more times with water then dried under vacuum overnight. The product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield. LCMS (M+1=318)
Aufarbeitung
- additionAfter the addition
- customThen, the reaction was quenched by addition to ice cold 6N NaOH
- additionThe mixture was diluted with water
- filtrationthe solid was collected by filtration
- washThe solid was washed several more times with water
- customthen dried under vacuum overnight
- customThe product, 3-((7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was collected as a solid in 37% yield
Quellen und Nachweise
- ORD-Eintrag
- ord-ec7904f84ae042659f8780f9759663a4
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08575177B2
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