Diisopropylethylamine → HCID 66955360, Verbindung

HRID 1399676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399676
Cl[C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.C(N(CC)C(C)C)(C)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[C:35]([O:42][CH3:43])[CH:34]=1.COCCOC.O>[Cl-].[Na+].O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:2]2[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:16])[N:5]=[C:4]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[C:35]([O:42][CH3:43])[CH:34]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 3858606(4-Chloro-2-methoxyphenyl)boronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Produkt 1

HCID 66955360HCID 66955360, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A suspension of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.239 g; 0.75 mmol), tetrakis(triphenylphosphine) palladium(0) (0.087 mg; 0.075 mmol), N,N-diisopropylethylamine (0.517 mL; 3 mmol) and 4-chloro-2-methoxyphenylboronic acid (0.210 g; 1.125 mmol) in a mixture DME-water (2 mL) was heated in a sealed tube for 2.5 h. The mixture was diluted with brine and extracted with ethyl acetate. The combined organics were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.190 g (60%) of the title compound as a colorless oil.

Aufarbeitung

  1. temperaturewas heated in a sealed tube for 2.5 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

Quellen und Nachweise

ORD-Eintrag
ord-9078a88b5a8f4d87b3048e35e0861892
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906906B2

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