Diisopropylethylamine → Ethyl {4-[((2-methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetate

HRID 1269629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269629
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.C(N(CC)C(C)C)(C)C.[CH3:30][O:31][CH2:32][CH2:33][NH:34][CH2:35][C:36]1[CH:48]=[CH:47][C:39]([O:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:38]([CH3:49])[CH:37]=1>C(Cl)Cl>[CH3:30][O:31][CH2:32][CH2:33][N:34]([CH2:35][C:36]1[CH:48]=[CH:47][C:39]([O:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:38]([CH3:49])[CH:37]=1)[C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 184483542-(Methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidineHCID 58622873Ethyl (4-{[(2-methoxyethyl)amino]methyl}-2-methylphenoxy)acetate

Produkt 1

HCID 58622875Ethyl {4-[((2-methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetateAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-(methylsulfonyl)-4-[4-(trifluoromethyl)phenyl]pyrimidine (0.2 g, 0.66 mmol), N,N-diisopropylethylamine (0.11 mL, 0.66 mmol) and ethyl (4-{[(2-methoxyethyl)amino]methyl}-2-methylphenoxy)acetate (0.28 g. 0.99 mmol) was heated at 100° C. in a sealed reactivial for 20 h. The reaction mixture was then allowed to come to room temperature, and the residue dissolved in CH2Cl2 (30 mL), the organic extract was washed water (20 mL) and passed through a hydrophobic frit before concentrating in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting 1:9 EtOAc:cyclohexane afforded the title compound as a pale yellow oil (0.08 g).

Aufarbeitung

  1. customto come to room temperature
  2. extractionthe organic extract
  3. washwas washed water (20 mL)
  4. concentrationbefore concentrating in vacuo
  5. customPurification by Biotage™ chromatography (Silica, 90 g)
  6. washeluting 1:9 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-452481601cb746aeb8e4d3fe65e20f3e
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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