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

HRID 1269648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269648
Cl[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[CH2:26]([NH:30][CH2:31][C:32]1[CH:44]=[CH:43][C:35]([O:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:34]([CH3:45])[CH:33]=1)[CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[CH2:26]([N:30]([CH2:31][C:32]1[CH:44]=[CH:43][C:35]([O:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:34]([CH3:45])[CH:33]=1)[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH2:27][CH2:28][CH3:29]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 184484054-Chloro-6-(4-methoxyphenyl)-5-methylpyrimidineHCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

Produkt 1

HCID 58622872Ethyl [4-({butyl[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino}methyl)-2-methylphenoxy]acetateAusbeute 18,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-6-(4-methoxyphenyl)-5-methylpyrimidine (0.164 g, 0.7 mmol), diisopropylethylamine (0.24 mL, 1.4 mmol) and ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (0.29 g, 1.05 mmol) was heated at 100° C. in a sealed reactivial for 18 h. The reaction mixture was then allowed to come to room temperature. The residue was dissolved in CH2Cl2 (50 mL), the organic solution was washed water (20 mL) and passed through a hydrophobic frit before concentrating in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting with 3:17–1:4 EtOAc:cyclohexane afforded the title compound as a pale yellow oil (62 mg).

Aufarbeitung

  1. customto come to room temperature
  2. washthe organic solution was washed water (20 mL)
  3. concentrationbefore concentrating in vacuo
  4. customPurification by Biotage™ chromatography (Silica, 90 g)
  5. washeluting with 3:17–1:4 EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-7176481261694e17beaf04d23c611de4
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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