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5-Bromo-4-methyl-1,3-thiazole → 7-(1-Ethyl-propyl)-2,5-dimethyl-3-(4-methyl-thiazol-5-yl)-pyrazolo[1,5-a]pyrimidine

HRID 1660741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1660741
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[CH3:7].[CH2:8]([CH:10]([C:13]1[N:18]2[N:19]=[C:20]([CH3:23])[C:21](I)=[C:17]2[N:16]=[C:15]([CH3:24])[CH:14]=1)[CH2:11][CH3:12])[CH3:9]>O1CCCC1.[Zn].Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:8]([CH:10]([C:13]1[N:18]2[N:19]=[C:20]([CH3:23])[C:21]([C:2]3[S:6][CH:5]=[N:4][C:3]=3[CH3:7])=[C:17]2[N:16]=[C:15]([CH3:24])[CH:14]=1)[CH2:11][CH3:12])[CH3:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 150209975-Bromo-4-methyl-1,3-thiazoleHCID 248985233-Iodo-2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 674287127-(1-Ethyl-propyl)-2,5-dimethyl-3-(4-methyl-thiazol-5-yl)-pyrazolo[1,5-a]pyrimidineAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysator2×
HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add Rieke® zinc (10 g in 100 mL of THF, 13.2 mL, 18.48 mmol) to 5-bromo-4-methylthiazole (2.13 g, 18.48 mmol) and heat at reflux for 2 h. Cool the mixture to room temperature and settle the zinc down by centrifuge. Bubble nitrogen gas through 7-(1-ethyl-propyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (900 mg, 2.62 mmol) in dry tetrahydrofuran (10 mL) and add the organozinc bromide solution followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (106 mg, 0.13 mmol). Stir the reaction mixture under reflux overnight and cool to room temperature. Add ammonium chloride solution to the reaction mixture and extract with dichloromethane. Dry the organic portion over sodium sulfate, filter, and remove the solvent under vacuum. Purify the crude product by silica gel column chromatography, elueting with hexane/ethyl acetate (3/1) to obtain the title compound (652 mg, 79%). 1H NMR (400 MHz, CDCl3): δ 8.80 (s, 1H), 6.48 (s, 1H), 3.63 (m, 1H), 2.57 (s, 3H), 2.43 (s, 3H), 2.40 (s, 3H), 1.85 (m, 4H), 0.90 (t, 6H, J=7.3Hz). ES/MS m/z 315 (M+1)+.

Aufarbeitung

  1. temperatureheat
  2. temperatureat reflux for 2 h
  3. temperatureunder reflux overnight
  4. temperaturecool to room temperature
  5. extractionAdd ammonium chloride solution to the reaction mixture and extract with dichloromethane
  6. dry with materialDry the organic portion over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under vacuum
  9. customPurify the crude product by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-718a48d476884e51a2b7c3b89c1b7d8c
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030304B2

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