2-Bromo-1,1-dimethoxyethane → 8-Chloroimidazo[1,2-a]pyrazine

HRID 1186458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186458
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([Cl:11])[C:5]2=[N:4][CH:3]=1.NC1C(Cl)=NC=CN=1.BrCC(OC)OC>>[Cl:11][C:10]1[C:5]2[N:6]([CH:2]=[CH:3][N:4]=2)[CH:7]=[CH:8][N:9]=1

Komponenten

4

Edukt 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 2762242-Amino-3-chloropyrazineHCID 100598493-Bromo-8-chloroimidazo[1,2-a]pyrazine

Produkt 1

HCID 102612868-Chloroimidazo[1,2-a]pyrazine

Versuchsvorschrift

The starting materials are either commercially available or can be synthesized by methods known in the art. Compounds of formula Ia where X is N can be synthesized starting from the known 3-bromo-8-chloro-imidazo[1,2-a]pyrazine (4). Lumma, Jr., W. C.; Randall, W. C.; Cresson, E. L.; Huff, J. R.; Hartman, R. D.; Lyon, T. F. J. Med. Chem. 1983, 26, 357-363. Meurer, L. C.; Tolman, R. L.; Chapin, E. W.; Saperstein, R.; Vicario, P. P.; Zrada, M. M.; MacCoss, M. J. Med. Chem. 1992, 35, 3845-3857. In accordance to Scheme 1 below, 2-amino-3-chloropyrazine (1) can be reacted with 2-bromo-1,1-dimethoxy-ethane (2) to give 8-chloro-imidazo[1,2-a]pyrazine (3) which can be brominated to give 3-bromo-8-chloro-imidazo[1,2-a]pyrazine (4). Compound 4 can be reacted with an appropriate amine (HNR1R2) either in excess or in the presence of another base, such as diisopropyl ethyl amine, in an appropriate solvent, such as ethanol or butanol, between room temperature to reflux to give compound 5. Compound 5 can than be condensed with 2-methylsulfanyl-4-tributylstannanyl-pyrimidine (6) in the presence of a suitable palladium catalyst to give intermediate 7.

Aufarbeitung

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Quellen und Nachweise

ORD-Eintrag
ord-f4274a20e8bb49af97cb15233eb2c9bd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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