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

HRID 16295

Reaction equation

HRID 16295 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]([F: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]([F: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 534860742-Chloro-6-(3-fluorophenoxy)pyrazine

Product 1

HCID 248795286-(3-fluorophenoxy)-N-(3,4,5-trimethoxyphenyl)pyrazin-2-amineYield 61%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using Method EE with 2-chloro-6-(3-fluorophenyloxy)-pyrazine (200 mg, 0.89 mmol) and 3,4,5-trimethoxyaniline (196 mg, 1.07 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:1), the title compound was obtained (200 mg). Yield: 61%. 1H NMR (250 MHz, DMSO-d6) δ 3.44 (s, 6H, [CH3O]3+5), 3.55 (s, 3H, [CH3O]4), 6.77 (s, 2H, Harom 2′+6′), 7.02-7.09 (m, 2H, Harom 4+6), 7.16 (d, 1H, Harom 2, JF=8.8 Hz), 7.43 (q, 1H, Harom 5, J=8.5 Hz), 7.78 (s, 1H, HPz 5), 7.98 (s, 1H, HPz 3), 9.61 (s, 1H, NH). m/z: 372.1 [(M+H)+, calcd for C19H18FN3O4 371.1].

Sources & evidence

ORD record
ord-67bf2d049ea44a6c92af680c60a7b4e7
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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