Triisopropyl borate → (5-Bromo-4-methyl-pyrimidin-2-yl)-bis-(4-methoxy-benzyl)-amine

HRID 912346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912346
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.[H-].[Na+].B(OC(C)C)(OC(C)C)OC(C)C.[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1.[C:40]1(C)[CH:45]=CC=[CH:42][CH:41]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([N:8]([CH2:42][C:41]2[CH:36]=[CH:35][C:39]([O:38][CH3:37])=[CH:45][CH:40]=2)[CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 21531Triisopropyl borateHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 186161965-Bromo-4-methylpyrimidin-2-amineHCID 22635083Tetrahydrofuran toluene

Produkt 1

HCID 67385432(5-Bromo-4-methyl-pyrimidin-2-yl)-bis-(4-methoxy-benzyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (5-bromo-4-methyl-pyrimidin-2-yl)-bis-(4-methoxy-benzyl)-amine (1.28 g) obtained through the reaction of 5-bromo-4-methyl-pyrimidin-2-ylamine and 4-methoxybenzyl chloride in DMF in the presence of 60% oily sodium hydride, and boric acid triisopropyl (1.94 ml) in THF/toluene (4.2 ml/17 ml), at −78° C., n-butyl lithium-hexane solution (1.6 M, 4.5 ml) was added dropwise, followed by stirring at −78° C. for 1 hour. To the reaction mixture, water (10 ml) was added, and a colorless precipitate resulting from the addition of concentrated HCl (500 μl) was filtered, to obtain 2-{bis-(4-methoxy-benzyl)-amino}-4-methyl-pyrimidin-5-boronic acid. Then, the resulting colorless precipitate (787 mg), pinacol (248 mg) and magnesium sulfate (248 mg) were stirred in dichloromethane (10 ml) for 1 hour, followed by filtering off insolubles, and the filtrate was concentrated under reduced pressure, to obtain bis-(4-methoxy-benzyl)-[4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-yl]-amine (275 mg, 29%) as a colorless amorphous.

Quellen und Nachweise

ORD-Eintrag
ord-cabaf786361b4ff0bfc66ec38f72c1c7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022205B2

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