Ethyl Acetate → 2-(N-(2-bromo-4-(2-propyl)phenyl)amino)-4-carbomethoxy-6-methylpyrimidine

HRID 1251509

Reaktionsgleichung

Reaktionsgleichung von HRID 1251509
Cl[C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Br:13][C:14]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:15]=1[NH2:16].C(OCC)(=O)C>O1CCOCC1>[Br:13][C:14]1[CH:20]=[C:19]([CH:21]([CH3:22])[CH3:23])[CH:18]=[CH:17][C:15]=1[NH:16][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 5213372-Bromo-4-isopropylanilineHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylate

Produkt 1

HCID 183237202-(N-(2-bromo-4-(2-propyl)phenyl)amino)-4-carbomethoxy-6-methylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-4-carbomethoxy-6-methylpyrimidine (47.0 g, 252 mmol) and 2-bromo-4-(2-propyl)aniline (54.0 g, 252 mmol) in dioxane (400 mL) was stirred at reflux temperature for 20 h under a nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and concentrated on a rotary evaporator. The residue was treated with a saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo to provide a red oil. Column chromatography (ethyl acetate:hexanes::1:1) gave the title product as a crude oil. Recrystallization from ether-hexanes, collection by filtration and drying in vacuo afforded the title compound as a solid (42.8 g, 17% yield): mp 75-76° C.; NMR (CDCl3, 300 MHz): 8.4 (d, 1H, J=8); 7.65 (br s, 1H), 7.4 (d, 1H, J=1), 7.3 (s, 1H), 7.2 (dd, 1H, J=8,1), 4.0 (s, 3H), 2.85 (septet, 1H, J=7), 2.5 (br s, 3H), 1.25 (d, 6H, J=7); Anal. (C16H18BrN3O2): C, 52.76, H, 4.98; N, 11.54; Br, 21.94; Found: C, 52.71; H, 4.99; N, 11.38; Br, 21.83.

Aufarbeitung

  1. temperatureat reflux temperature for 20 h under a nitrogen atmosphere
  2. concentrationconcentrated on a rotary evaporator
  3. additionThe residue was treated with a saturated sodium bicarbonate solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customSolvent was removed in vacuo
  8. customto provide a red oil

Quellen und Nachweise

ORD-Eintrag
ord-f94eea9d2cff4539aa94f18b952f7b12
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342503B1

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