Dimethylformamide → 5-(5-Chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 2037042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037042
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][CH:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[CH3:18])[N:12]3[N:25]=[CH:26][CH:27]=[C:11]3[N:10]=2)[CH:7]=1.P(Cl)(Cl)(Cl)=O.CN([CH:37]=[O:38])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][CH:17]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[CH3:18])[N:12]3[N:25]=[CH:26][C:27]([CH:37]=[O:38])=[C:11]3[N:10]=2)[CH:7]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 58314469HCID 58314469, Verbindung

Produkt 1

HCID 583140035-(5-Chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehydeAusbeute 41 %

Versuchsvorschrift

In a reaction flask, N5-(5-chloro-2-fluorophenyl)-N7-(2-morpholinopropyl)pyrazolo[1,5-a]pyrimidine-5,7-diamine (84 mg, 0.21 mmol) was dissolved in DMF (0.9 mL) then phosphorous oxychloride (58 uL, 0.62 mmol) was added slowly at room temperature. The reaction mixture was allowed to stir at room temperature for 2 days then quenched by addition to 6N NaOH solution. The pH of the mixture was adjusted with 6N HCl to pH=7-9. The solid was recovered by filtration and washed with water. The product, 5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was purified by preparative TLC (5% acetone/dichloromethane) to yield 37 mg of the desired product (41% yield). LCMS (M+1=433)

Aufarbeitung

  1. customthen quenched by addition to 6N NaOH solution
  2. filtrationThe solid was recovered by filtration
  3. washwashed with water
  4. customThe product, 5-(5-chloro-2-fluorophenylamino)-7-(2-morpholinopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde, was purified by preparative TLC (5% acetone/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-fe85ac5b30654090b59730985b14be45
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

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