3,4,5-Trimethoxyaniline → 2-(3,4,5-Trimethoxyphenylamino)-6-[(4-phenyl)-phenyl-oxy]-pyrazine

HRID 16300Notes

Reaction equation

HRID 16300 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26]>CCOC(C)=O>[CH3:33][O:32][C:28]1[CH:27]=[C:25]([NH:26][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:11][CH:10]=3)[N:3]=2)[CH:24]=[C:23]([O:22][CH3:21])[C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 593434952-Chloro-6-(4-phenyl-phenyl-oxy)-pyrazine

Product 1

HCID 593434832-(3,4,5-Trimethoxyphenylamino)-6-[(4-phenyl)-phenyl-oxy]-pyrazineYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-[(4-phenyl)-phenyl-oxy]-pyrazine (110 mg, 0.39 mmol) and 3,4,5-trimethoxyaniline (84 mg, 0.46 mmol), and purification by column chromatography (AcOEt), the title compound was obtained (105 mg). Yield: 63%. 1H NMR (250 MHz, DMSO-d6) δ 3.38 (s, 6H, [CH3O]3+5), 3.52 (s, 3H, [CH3O]4), 6.81 (s, 2H, Harom2′+6′), 7.29 (d, 2H, Harom 3+5, J=8.6 Hz), 7.36-7.53 (m, 1H, Harom4″), 7.68 (d, 2H, Harom 2″+6″, J=7.9 Hz), 7.71 (d, 2H, Harom 2+6, J=8.7 Hz), 7.81 (s, 1H, HPz 5), 7.98 (s, 1H, HPz 3), 9.58 (s, 1H, NH). m/z: 430.2 [(M+H)+, calcd for C25H23N3O4 429.2].

Sources & evidence

ORD record
ord-40cc64b7379e40a78d85afc939652786
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

Loading…