3,4,5-Trimethoxyaniline → 6-(3-chlorophenoxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amine

HRID 16297Notes

Reaction equation

HRID 16297 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[NH2:21]>CCOC(C)=O.C1CCCCC1>[CH3:28][O:27][C:23]1[CH:22]=[C:20]([NH:21][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=3)[N:3]=2)[CH:19]=[C:18]([O:17][CH3:16])[C:24]=1[O:25][CH3:26]

Participants

5

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 202879982-Chloro-6-(3-chlorophenyl-oxy)-pyrazine

Product 1

HCID 248792636-(3-chlorophenoxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amineYield 43%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-(3-chlorophenyloxy)-pyrazine (200 mg, 0.83 mmol) and 3,4,5-trimethoxyaniline (183 mg, 1.00 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:1), the title compound was obtained (165 mg). Yield: 43%. 1H NMR (250 MHz, DMSO-d6) δ 3.43 (s, 6H, [CH3O]3+5), 3.54 (s, 3H, [CH3O]4), 6.76 (s, 2H, Harom2′+6′), 7.18 (d, 1H, Harom 4, J=6.5 Hz), 7.28 (d, 1H, Harom 6, J=6.7 Hz), 7.36 (s, 1H, Harom 2), 7.43 (t, 1H, Harom 5, J=8.1 Hz), 7.79 (s, 1H, HPz 5), 7.98 (s, 1H, HPz 3), 9.62 (s, 1H, NH).

Sources & evidence

ORD record
ord-2350f0e970c24e93a7774b12ed461511
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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