Potassium phosphate, tribasic, monohydrate → (5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

HRID 1913255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913255
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27](I)=[C:4]2[N:3]=1.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC.O.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]>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:31]3[CH:30]=[N:29][C:38]4[C:33]([CH:32]=3)=[CH:34][CH:35]=[CH:36][CH:37]=4)=[C:4]2[N:3]=1

Komponenten

7

Edukt 3

HCID 22031701Potassium phosphate, tribasic, monohydrateHCID 22173501Quinoline-2-boronic acidHCID 772312185-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine

Produkt 1

HCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To crude 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-10b, 7.1 g) in DME (120 mL) and H2O (15 mL) were added the quinoline boronic acid (2.4 g, 14.1 mmol), PdCl2(dppf)2 (1.0 g, 1.2 mmol) and K3PO4.H2O (5.4 g, 25.6 mmol). The reaction mixture was heated at 60° C. for 2 hours, at which time LC/MS analysis confirmed full consumption of starting material. On cooling, H2O (40 mL) and EtOAc (100 mL) were added and organics were extracted with EtOAc (4×50 mL), dried (Na2SO4), and concentrated in vacuo to give a brown oil. Gradient column chromatography on silica eluting with 10% to 60% EtOAc/hexanes gave 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-10b) as a light yellow solid (4.1 g, 7.4 mmol, 65% over three steps).

Aufarbeitung

  1. customconsumption of starting material
  2. temperatureOn cooling
  3. additionH2O (40 mL) and EtOAc (100 mL) were added
  4. extractionorganics were extracted with EtOAc (4×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-b859381930624c7aa80dad6079d7dd4a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609675B2

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