3-Aminophenylboronic acid → 2-(3,4,5-Trimethoxyphenylamino)-6-(3-aminophenyl)pyrazine

HRID 16252

Reaction equation

HRID 16252 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].[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:21])[CH:27]=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Product 1

HCID 115594032-(3,4,5-Trimethoxyphenylamino)-6-(3-aminophenyl)pyrazineYield 38.6%

Procedure

Using Method C with 1.0 g (3.4 mmol) 2a and 635 mg (4.1 mmol) 3-aminophenyl boronic acid, 463 mg pure title compound were obtained. The filtrate was submitted to purification by preparative HPLC (eluent:AcOEt) and another fraction of 412 mg was obtained. A total of 875 mg CJS 364 (72.9%) were obtained. Reaction time: 28 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.64 (s, 3H, CH3O(4′)), 3.81 (s, 6H, CH3O(3′+5′)), 5.19 (s, 2H, NH2), 6.66 (d, 1H, Harom 4′, J=7.70), 7.13 (t, 1H, Harom 5′, J=7.77), 7.22 (d, 1H, Harom 6′), 7.26 (s, 2H, Harom(2+6)), 7.29 (s, 1H, Harom 2′), 8.11 (s, 1H, HP5), 8.33 (s, 1H, HP3), 9.51 (s, 1H, NHamine);

Sources & evidence

ORD record
ord-7453702616c54593bf58545c50d6c240
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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