Acetic Acid → N-(3-bromo-5-methylphenyl)-4-(propan-2-yl)-pyrimidin-2-amine

HRID 1040057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040057
C(O)(=O)C.Cl[C:6]1[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][N:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[NH2:19]>O1CCOCC1>[Br:15][C:16]1[CH:17]=[C:18]([NH:19][C:6]2[N:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][N:7]=2)[CH:20]=[C:21]([CH3:23])[CH:22]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 30185263-Bromo-5-methylanilineHCID 249019162-Chloro-4-isopropylpyrimidine

Produkt 1

HCID 67248097N-(3-bromo-5-methylphenyl)-4-(propan-2-yl)-pyrimidin-2-amineAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Acetic acid (0.192 mL, 3.35 mmol) was added to commercially available 2-chloro-4-(propan-2-yl)pyrimidine (0.5 g, 3.19 mmol) and 3-bromo-5-methylaniline (0.900 g, 3.19 mmol) suspended in dioxane (6.39 mL). Reaction was heated to 120° C. (bath temp) overnight. Then, the reaction was cooled to room temperature and purified by column chromatography on silica gel eluting with ethyl acetate and hexanes to give N-(3-bromo-5-methylphenyl)-4-(propan-2-yl)-pyrimidin-2-amine (959.8 mg, 3.13 mmol, 98%) as a white solid.

Aufarbeitung

  1. customReaction
  2. temperatureThen, the reaction was cooled to room temperature
  3. custompurified by column chromatography on silica gel eluting with ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-50cc06cacf6e42628e60dc22f68cdc50
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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