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

HRID 16308Notes

Reaction equation

HRID 16308 reaction equation
[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:27]=[CH:26][N:25]=[CH:24][CH:23]=1>>[N:25]1[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][CH:24]=1

Participants

3

Reactant 2

HCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazineHCID 178418642HCID 178418642, compound

Product 1

HCID 248793946-(Pyridin-4-yloxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amineYield 50%

Procedure

Using Method X with 150 mg of 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine and 4-hydroxypyridine, the title compound was obtained (89 mg). Yield: 50%. 1H NMR (250 MHz, DMSO-d6) δ 3.64 (s, 3H), 3.79 (s, 6H), 6.29 (d, 2H, J=7.9 Hz), 7.07 (s, 2H), 8.19 (s, 1H), 8.32 (s, 1H), 8.43 (d, 2H, J=8.0 Hz), 9.91 (bs, 1H). 13C NMR (62.9 MHz, DMSO-d6) δ 55.61, 60.11, 96.50, 117.94, 121.98, 132.71, 132.79, 135.77, 136.52, 145.43, 150.31, 152.85, 178.22. m/z 355.1 [(M+H)+ calcd for C18H18N4O4 354.1].

Sources & evidence

ORD record
ord-54f08182d6034e6d9bd403a29aca9e62
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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