Cesium carbonate → 2-(2-Methoxy-ethylamino)-5-(pyrimidin-5-ylamino)-pyrimidine-4-carboxylic acid ethyl ester

HRID 2368336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2368336
[CH2:1]([O:3][C:4]([C:6]1[C:11](Br)=[CH:10][N:9]=[C:8]([NH:13][CH2:14][CH2:15][O:16][CH3:17])[N:7]=1)=[O:5])[CH3:2].[NH2:18][C:19]1[CH:20]=[N:21][CH:22]=[N:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH:18][C:19]2[CH:20]=[N:21][CH:22]=[N:23][CH:24]=2)=[CH:10][N:9]=[C:8]([NH:13][CH2:14][CH2:15][O:16][CH3:17])[N:7]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 344373Pyrimidin-5-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58368043Ethyl 5-bromo-2-((2-methoxyethyl)amino)pyrimidine-4-carboxylate

Produkt 1

HCID 700975102-(2-Methoxy-ethylamino)-5-(pyrimidin-5-ylamino)-pyrimidine-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A microwave reaction tube was charged with a suspension of 5-bromo-2-(2-methoxy-ethylamino)-pyrimidine-4-carboxylic acid ethyl ester (30 mg, 0.1 mmol), 5-aminopyrimidine (14 mg, 0.15 mmol) and cesium carbonate (45 mg, 0.14 mmol) in dioxane (0.6 ml) and flushed with argon. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 19 mg, 32 μmol) and tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (10 mg, 10 μmol) were consecutively added and the reaction tube was sealed and stirred overnight at 130° C. After cooling-down to ambient temperature, the reaction mixture was filtrated. The filtrate was concentrated in vacuo and the product was obtained after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (11 mg, 35%).

Aufarbeitung

  1. customA microwave reaction tube
  2. customflushed with argon
  3. customthe reaction tube was sealed
  4. filtrationAfter cooling-down to ambient temperature, the reaction mixture was filtrated
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe product was obtained
  7. customafter purification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-830ddd46a7074f21a616bc4a08d42c58
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703768B2

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