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2-Trimethylsilylthiazole → 2,5-Dimethyl-7-(1-propyl-butyl)-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine

HRID 1660739
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660739
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.C([Li])CCC.[CH2:15]([CH:18]([C:22]1[N:27]2[N:28]=[C:29]([CH3:32])[C:30](I)=[C:26]2[N:25]=[C:24]([CH3:33])[CH:23]=1)[CH2:19][CH2:20][CH3:21])[CH2:16][CH3:17]>C1COCC1.[Cl-].[Zn+2].[Cl-].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]>[CH3:32][C:29]1[C:30]([C:5]2[S:4][CH:3]=[N:7][CH:6]=2)=[C:26]2[N:25]=[C:24]([CH3:33])[CH:23]=[C:22]([CH:18]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:16][CH3:17])[N:27]2[N:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 5884532-TrimethylsilylthiazoleHCID 248985247-(1-Propyl-butyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 674278072,5-Dimethyl-7-(1-propyl-butyl)-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidineAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855
Zincchloride
Katalysator
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Charge an oven dried flask with 2-trimethylsilanylthiazole (1.765 g, 11.24 mmol) dissolved in anhydrous THF (30 mL) and chill under an inert atmosphere to −78° C. Slowly add n-butyl lithium (2.5 M hexane solution, 4.5 mL, 11.24 mmol) and stir 30 min at −78° C. Add anhydrous zinc chloride (2.26 g, 16.58 mmol) in one aliquot and stir 30 min at −78° C. Allow the reaction to rise to room temperature, stir 30 min, and add 7-(1-propyl-butyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (1.624 g, 5.18 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (0.423 g, 0.518 mmol). Reflux overnight in an oil bath (90° C.) under an inert atmosphere. Cool the reaction to room temperature, quench with saturated sodium bicarbonate, and dilute with ethyl acetate (150 mL). Separate and extract the aqueous with ethyl acetate (75 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% hexane/0% (30% THF/hexane) to 0% hexane/100% (30% THF/hexane) in a step gradient of 10% increments to give a white solid (0.720 g, 42%). ES/MS m/z 329.0 (M+1)+.

Aufarbeitung

  1. additionCharge an oven
  2. customthe reaction
  3. customto rise to room temperature
  4. temperatureReflux overnight in an oil bath (90° C.) under an inert atmosphere
  5. temperatureCool
  6. customthe reaction to room temperature
  7. customquench with saturated sodium bicarbonate
  8. additiondilute with ethyl acetate (150 mL)
  9. customSeparate
  10. extractionextract the aqueous with ethyl acetate (75 mL)
  11. dry with materialCombine the organic phases, dry over anhydrous magnesium sulfate
  12. filtrationfilter
  13. concentrationconcentrate under reduced pressure
  14. customPurify the resulting residue
  15. washeluting with 100% hexane/0% (30% THF/hexane) to 0% hexane/100% (30% THF/hexane) in a step gradient of 10% increments

Quellen und Nachweise

ORD-Eintrag
ord-4643d4c65952478886d7f763cc52ec94
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030304B2

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