3-Pyridinylboronic acid → 6-(pyridin-3-yl)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amine

HRID 16255

반응식

HRID 16255 반응식
[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].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=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:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

참가 물질

3

반응물 2

HCID 27343783-Pyridinylboronic acidHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

생성물 1

HCID 248793306-(pyridin-3-yl)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amine수율 52.2%

실험 절차

Using Method C with 200 mg (0.68 mmol) 2a and 100 mg (0.82 mmol) 3-pyridylboronic acid, 120 mg (52.1%) pure title compound were obtained after purification of the whole batch by column chromatography (Kieselgel 60, 0.040-0.063; eluent: AcOEt:MeOH 1:1). Reaction time: 3 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.67 (s, 3H, CH3O(4′)), 3.85 (s, 6H, CH3O(3′+5′)), 7.26 (s, 2H, Harom(2+6)), 7.59 (m, 1H, Harom 5′), 8.25 (s, 1H, HP5), 8.49 (d, 1H, Harom 6′, J=7.90), 8.63 (s, 1H, HP3), 8.69 (d, 1H, Harom 4′, J=3.18), 9.51 (d, 1H, Harom 2′, J=2.21), 9.51 (s, 1H, NHamine); MS, (C18H18N4O3), m/z: 339.1 [M++1, 100].

출처 및 근거

ORD 기록
ord-8661fc380750426bb2b1da2699c717b7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737152B2

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