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Cesium carbonate → Ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate

HRID 2284653
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2284653
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=1.Br[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.[Pd].[Pd]>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([NH:1][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][N:3]=2)=[CH:19][CH:20]=1)#[N:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-HCID 90052100Ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate

Produkt 1

HCID 90052034Ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylateAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of tris(dibenzylideneacetone)dipalladium(0) (1.14 g) and 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (1.45 g) in 1,4-dioxane (150 mL), ethyl 2-amino-4-(propylamino)pyrimidine-5-carboxylate (C3, 5.61 g), 4-bromobenzonitrile (6.83 g) and cesium carbonate (24.40 g) were added at room temperature, and the mixture was stirred at 100° C. for 11 hours and 30 minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, then the insoluble matter was removed by filtration through Cerite, and then 1.0 mol/L aqueous hydrochloric acid and ethyl acetate were added. The organic layer was separated, washed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate was added, and the solid matter was taken by filtration to obtain ethyl 2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (C4, 2.68 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matter was removed by filtration through Cerite
  3. addition1.0 mol/L aqueous hydrochloric acid and ethyl acetate were added
  4. customThe organic layer was separated
  5. washwashed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue, ethyl acetate was added
  9. filtrationthe solid matter was taken by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e492db74e3c947e6ac17c4bd427ab7fb
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145415B2

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