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3-Aminopyridine → 5-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid ethyl ester

HRID 1012185
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1012185
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+].[CH2:49]([O:51][C:52]([C:54]1[S:55][C:56]([C:59]2[CH:64]=[CH:63][N:62]=[C:61](Cl)[N:60]=2)=[CH:57][CH:58]=1)=[O:53])[CH3:50].[NH2:66][C:67]1[CH:68]=[N:69][CH:70]=[CH:71][CH:72]=1>O1CCOCC1.CCOC(C)=O.O.CC(O)=O.CC(O)=O.[Pd]>[CH2:49]([O:51][C:52]([C:54]1[S:55][C:56]([C:59]2[CH:64]=[CH:63][N:62]=[C:61]([NH:66][C:67]3[CH:68]=[N:69][CH:70]=[CH:71][CH:72]=3)[N:60]=2)=[CH:57][CH:58]=1)=[O:53])[CH3:50]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 100093-AminopyridineHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 594684545-(2-Chloro-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester

Produkt 1

HCID 594686225-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid ethyl ester
Ausbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 4144353Palladium (II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Palladium II acetate (8.3 mg, 0.1 mmol) and xantphos 42.8 mg, 0.2 mmol) were precombined in 4 mL dry dioxane under nitrogen gas. Potassium carbonate (1.03 g, 7.46 mmol) was added followed by a solution of 5-(2-Chloro-pyrimidin-4-yl)-thiophene-2-carboxylic acid ethyl ester (100 mg, 0.373 mmol) and 3-aminopyridine (42 mg, 0.447 mmol) in 3 mL dioxane. The reaction was heated in a capped vial at 100° C. for 20 h. The cooled reaction mixture was diluted with EtOAc and water and the layers were separated. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was redissolved in ethyl ether and treated with 2 M HCl in ether to generate a precipitate which was collected by filtration to afford 76 mg (56.3%) of the title compound. The crude material was used in the next step.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was redissolved in ethyl ether
  6. additiontreated with 2 M HCl in ether
  7. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dc23e332563f4fb4bbb05c3fd47ca62e
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07977481B2

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