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

HRID 1269647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269647
Cl[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:28]([NH:32][CH2:33][C:34]1[CH:46]=[CH:45][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:36]([CH3:47])[CH:35]=1)[CH2:29][CH2:30][CH3:31]>C(Cl)Cl>[CH2:28]([N:32]([CH2:33][C:34]1[CH:46]=[CH:45][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:36]([CH3:47])[CH:35]=1)[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH2:29][CH2:30][CH3:31]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 184484034-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]PyrimidineHCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

Produkt 1

HCID 58622901Ethyl {4-[(butyl{5-methyl-6-[4-(trifluoromethyl)phenyl] pyrimidin-4-yl}amino)methyl]-2-methylphenoxy}acetateAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidine (0.229 g, 0.84 mmol), N,N-diisopropylethylamine (0.293 mL, 1.68 mmol) and ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (0.35 g, 1.26 mmol) was heated at 100° C. in a sealed reactivial for 18 h. The reaction mixture was then allowed to come to room temperature, and the residue dissolved in CH2Cl2 (50 mL), the organic extract was washed water (20 mL) and passed through a hydrophobic frit then concentrated in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting with 1:19–1:9 EtOAc:cyclohexane afforded the title compound as a colourless oil (0.19 g).

Aufarbeitung

  1. customto come to room temperature
  2. extractionthe organic extract
  3. washwas washed water (20 mL)
  4. concentrationthen concentrated in vacuo
  5. customPurification by Biotage™ chromatography (Silica, 90 g)
  6. washeluting with 1:19–1:9 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b68f11fdb84f43ccb1ecad7f2b41040e
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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