Thionyl Chloride → 1-[(6-Methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896417
O[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].S(Cl)(Cl)=O.[CH3:16][C:17]1[CH:18]=[N:19][C:20]2[N:21]([N:23]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:25]=2)[CH:22]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[CH3:16][C:17]1[CH:18]=[N:19][C:20]2[N:21]([N:23]=[C:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:25]=2[CH2:2][N:3]2[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]2=[O:11])[CH:22]=1

Komponenten

6

Edukt 4

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 577430576-Methyl-2-phenylpyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 536291271-[(6-Methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (3.18 mmol, 1 eq, 0.5 g) in toluene (20 ml) is added thionyl chloride (3.5 mmol, 1.1 eq, 0.416 g). The mixture is stirred vigorously overnight at 80° C. After this time, 6-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x122 (3.18 mmol, 1 eq, 0.665 g) and AlCl3 (3.18 mmol, 1 eq, 0.424 g) are successively added. The mixture is stirred at 80° C. for 2 hours. After evaporation of the solvent under reduced pressure, the crude mixture is poured to water and extracted with dichloromethane. The cumulated organic layers are dried over MgSO4, filtered over celite and evaporated under reduced pressure. The crude reaction mixture is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v)) and crystallized with AcOEt to afford 0.5 g of 1-[(6-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-3-yl)methyl]-4-propylpyrrolidin-2-one 202.

Aufarbeitung

  1. stirringThe mixture is stirred at 80° C. for 2 hours
  2. customAfter evaporation of the solvent under reduced pressure
  3. additionthe crude mixture is poured to water
  4. extractionextracted with dichloromethane
  5. dry with materialThe cumulated organic layers are dried over MgSO4
  6. filtrationfiltered over celite
  7. customevaporated under reduced pressure
  8. customThe crude reaction mixture
  9. customis purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v))
  10. customcrystallized with AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-114a0710b86e40b8b913e682471cc5fa
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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