3-Hydroxypyridine → 6-(Pyridin-3-yloxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amine

HRID 16309

Reaktionsgleichung

Reaktionsgleichung von HRID 16309
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][C:16]2[N:15]=[C:14]([NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[CH:19]=[N:18][CH:17]=2)[CH:23]=1

Komponenten

3

Edukt 2

HCID 79713-HydroxypyridineHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Produkt 1

HCID 248792066-(Pyridin-3-yloxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amineAusbeute 26 %

Versuchsvorschrift

Using Method X with 150 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine and 3-hydroxypyridine, the title compound was obtained (46 mg). Yield: 26%. 1H NMR (250 MHz, DMSO-d6) δ 3.41 (s, 6H), 3.54 (s, 3H), 6.71 (s, 2H), 7.47 (ddd, 1H, J1=0.6 Hz, J2=4.7 Hz, J3=8.4 Hz), 7.69 (ddd, 1H, J1=1.4 Hz, J2=2.8 Hz, J3=8.4 Hz), 7.82 (s, 1H), 7.98 (s, 1H), 8.43 (dd, 1H, J1=1.4 Hz, J2=4.7 Hz), 8.54 (dd, 1H, J1=0.5 Hz, J2=2.8 Hz), 9.61 (s, 1H). 13C NMR (62.9 MHz, DMSO-d6) δ 55.32, 60.04, 95.95, 120.94, 124.52, 128.42, 128.91, 132.34, 136.10, 142.68, 145.66, 150.31, 150.38, 152.71, 156.84. m/z 355.1 [(M+H)+ calcd for C18H18N4O4 354.1].

Quellen und Nachweise

ORD-Eintrag
ord-2745ade71a36470b9c18b908d39569ea
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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