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Water → [6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

HRID 1396170
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1396170
C(OC(=O)[N:7]([C:38]1[CH:39]=[N:40][C:41](Cl)=[CH:42][CH:43]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:36])[C:15]2[C:23]3[C:22]([O:24][CH3:25])=[N:21][CH:20]=[N:19][C:18]=3[N:17]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH:16]=2)=[C:10]([F:37])[N:9]=1)(C)(C)C.ClCCl.[CH:49]1([Mg]Br)[CH2:51][CH2:50]1.O>C1(C)C=CC=CC=1.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]>[CH:49]1([C:41]2[N:40]=[CH:39][C:38]([NH:7][C:8]3[N:9]=[C:10]([F:37])[C:11]([CH:14]([C:15]4[C:23]5[C:22]([O:24][CH3:25])=[N:21][CH:20]=[N:19][C:18]=5[N:17]([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:32])[CH3:31])[CH:16]=4)[OH:36])=[CH:12][CH:13]=3)=[CH:43][CH:42]=2)[CH2:51][CH2:50]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 58485805(6-chloro-pyridin-3-yl)-{6-fluoro-5-[hydroxy-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl esterHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 67445534
[6-(6-cyclopropyl-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol
Ausbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To (6-chloro-pyridin-3-yl)-{6-fluoro-5-[hydroxy-(4-methoxy-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester (72, 105 mg, 0.160 mmol) in 3.8 mL of toluene, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (13.0 mg, 0.016 mmol) is added under an atmosphere of nitrogen. The reaction is stirred for 5 minutes, then cyclopropylmagnesium bromide (17, 1.60 mL, 1.0 M in tetrahydrofuran, 1.60 mmol) is added slowly. The reaction is heated at 65° C. for 5 hours, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (73, 70 mg). MS (ESI) [M+H+]+=563.6.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ecb3dca4a75a4df98c6a168d390aeff7
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901118B2

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