StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Ethyl Acrylate → HCID 178471090, Verbindung

HRID 641699
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 641699
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[C:5](Br)=[C:4]([CH3:20])[N:3]=1.[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@@H:12]([O:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]2)[C:5](/[CH:23]=[CH:22]/[C:21]([O:25][CH2:26][CH3:27])=[O:24])=[C:4]([CH3:20])[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 8821Ethyl AcrylateHCID 178433368HCID 178433368, Verbindung

Produkt 1

HCID 178471090HCID 178471090, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a sealed tube a solution of 2-(cis-4-(2-amino-5-bromo-6-methylpyrimidin-4-ylamino)cyclohexyloxy)ethanol (695 mg, 4.03 mmol) and ethyl acrylate (438 uL, 4.03 mmol) in triethylamine (10 mL) was bubbled with argon for ˜5 minutes. Tetrakis(triphenylphosphin)-palladium (0) (232 mg, 0.201 mmol) was added, the vial was sealed and the mixture was bubbled again with argon (5 minutes). The reaction was heated to 130° C. overnight, cooled to room temperature and concentrated. The residue was dissolved in chloroform (500 mL) and washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-4%) to afford the title compound (615 mg, 84%).

Aufarbeitung

  1. customthe vial was sealed
  2. customthe mixture was bubbled again with argon (5 minutes)
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in chloroform (500 mL)
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography
  11. washeluting with chloroform/7 N ammonia in methanol (0-4%)

Quellen und Nachweise

ORD-Eintrag
ord-525b45e011d34169a8bda223f46ce51d
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07696213B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion