Diisopropylethylamine → Methyl 2-(4-methyl-6-(naphthalen-2-yl)-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399634
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.[CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1B(O)O>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>[CH3:16][C:6]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:2]([C:33]2[CH:34]=[CH:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:32]=2)[N:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:5]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 2734375(Naphthalen-2-yl)boronic acidHCID 86665652Methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

Produkt 1

HCID 66955496Methyl 2-(4-methyl-6-(naphthalen-2-yl)-2-phenylpyrimidin-5-yl)pentanoateAusbeute 71,6 %

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-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol), tetrakis(triphenylphosphine) palladium(0) (0.058 mg; 0.05 mmol), N,N-Diisopropylethylamine (0.345 mL; 2 mmol) and naphthalen-2-ylboronic acid (0.258 g; 1.5 mmol) in DME-water (2 mL) for 30 min. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.147 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 (2-40%) in heptane

Quellen und Nachweise

ORD-Eintrag
ord-6ecd724fc9714c3eaae826d4b704bb2c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906906B2

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