Diisopropylethylamine → Ethyl (2-methyl-4-{[{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}(propyl)amino]methyl}phenoxy)acetate

HRID 1269659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269659
[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][NH:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)C(C)C)(C)C.Cl[C:30]1[C:35]([CH3:36])=[C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[N:33]=[CH:32][N:31]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][N:16]([C:30]2[C:35]([CH3:36])=[C:34]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:41][CH:42]=3)[N:33]=[CH:32][N:31]=2)[CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 184484034-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]PyrimidineHCID 58622861Ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate

Produkt 1

HCID 58622851Ethyl (2-methyl-4-{[{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}(propyl)amino]methyl}phenoxy)acetateAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl {2-methyl-4-[(propylamino)methyl]phenoxy}acetate (0.279 g, 1.05 mmol), N,N-diisopropylethylamine (0.24 mL, 1.4 mmol) and 4-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (0.191 g, 0.7 mmol) were heated at 100° C. in a sealed reactivial for 18 h. After this time the reactivial was allowed to cool to room temperature and the residue dissolved in CH2Cl2 (50 mL) and washed with water (20 mL). The organic extract was separated by hydrophobic frit and evaporated. Purification by Biotage™ chromatography (Si, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (159 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed with water (20 mL)
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customevaporated
  6. customPurification by Biotage™ chromatography (Si, 40 g)
  7. washeluting 9:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-d52761d1af5047b6bb76e41a706a60cf
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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