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3-Iodo-2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidine → 3-(3-Methyl-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1639657
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1639657
[Br-].[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[Zn+].[CH2:9]([CH:11]([C:14]1[N:19]2[N:20]=[C:21]([CH3:24])[C:22](I)=[C:18]2[N:17]=[C:16]([CH3:25])[CH:15]=1)[CH2:12][CH3:13])[CH3:10]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:22]1[C:21]([CH3:24])=[N:20][N:19]2[C:14]([CH:11]([CH2:9][CH3:10])[CH2:12][CH3:13])=[CH:15][C:16]([CH3:25])=[N:17][C:18]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 248985233-Iodo-2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidineHCID 178429658HCID 178429658, Verbindung

Produkt 1

HCID 248987423-(3-Methyl-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Charge an oven dried flask with 3-methyl-2-thienylzinc bromide (11.0 mL, 5.5 mmol), anhydrous THF (6.0 mL) and 7-(1-ethyl-propyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (0.536 g, 1.56 mmol). Degas for 10-15 min with positive argon pressure and add dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (0.12 g, 0.15 mmol). Reflux overnight in an oil bath (100° C.) under an inert atmosphere. Cool the reaction to room temperature, quench with saturated ammonium chloride, and dilute with ethyl acetate (75 mL). Separate and extract the aqueous portion with ethyl acetate (50 mL). Combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue using flash chromatography, eluting with 100% pentane/0% (25% ethyl acetate/pentane) to 0% pentane/100% (25% ethyl acetate/pentane) in a step gradient of 10% increments to give a white foam. Triturate with hexane and filter. (0.432 g, 8%). 1H NMR (400 MHz, CDCl3): 7.26 (d, J=4.8, MHz, 1H), 6.96 (d, J=5.3 Hz, 1H), 6.42 (s, 1H), 3.64-3.60 (m, 1H), 2.53 (s, 3H), 2.43 (s, 3H), 2.14 (s, 3H), 1.87-1.79 (m, 4H), 0.88 (t, J=7.0 Hz, 6H).

Aufarbeitung

  1. additionCharge an oven
  2. customDegas for 10-15 min with positive argon pressure
  3. temperatureCool
  4. customthe reaction to room temperature
  5. customquench with saturated ammonium chloride
  6. additiondilute with ethyl acetate (75 mL)
  7. customSeparate
  8. extractionextract the aqueous portion with ethyl acetate (50 mL)
  9. dry with materialCombine the organic phases, dry over anhydrous magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under reduced pressure
  12. customPurify the resulting residue
  13. washeluting with 100% pentane/0% (25% ethyl acetate/pentane) to 0% pentane/100% (25% ethyl acetate/pentane) in a step gradient of 10% increments
  14. customto give a white foam
  15. customTriturate with hexane
  16. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-ed85291c60714ed2bce19877ebc9ad50
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08110580B2

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