Diisopropylethylamine → Methyl 2-(4-(4-isopropylphenyl)-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

HRID 1399703

Reaktionsgleichung

Reaktionsgleichung von HRID 1399703
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]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=1.C(N(CC)C(C)C)(C)C.[CH:32]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)([CH3:34])[CH3:33]>COCCOC.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>[CH:32]([C:35]1[CH:40]=[CH:39][C:38]([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]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:3]=2)=[CH:37][CH:36]=1)([CH3:34])[CH3:33]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27734804-Isopropylphenylboronic acidHCID 86665653Methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

Produkt 1

HCID 50995729Methyl 2-(4-(4-isopropylphenyl)-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Versuchsvorschrift

This compound was prepared according to general method E from methyl 2-(4-chloro-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.081 g; 0.25 mmol), tetrakis(triphenylphosphine) palladium(0) (0.029 g; 0.025 mmol), N,N-diisopropylethylamine (0.172 mL; 1.00 mmol) and 4-isopropylphenylboronic acid (0.082 g; 0.500 mmol) in DME-water (1 mL) for 20 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane furnished 0.074 g (71%) of the title compound.

Aufarbeitung

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (1-10%) in heptane

Quellen und Nachweise

ORD-Eintrag
ord-998d635ccd304c15be89c534f9797002
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906906B2

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