1,2-Dimethoxyethane → 2-Pyrazinamine, 5-(3-methoxyphenyl)-

HRID 719986Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[NH2:12][C:13]1[CH:18]=[N:17][C:16](Br)=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:16]2[N:17]=[CH:18][C:13]([NH2:12])=[N:14][CH:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Nitrogen was bubbled through a solution of 3-methoxyphenyl boronic acid (393 mg, 2.59 mmol), 2-amino-5-bromopyrazine (300 mg, 1.72 mmol), sodium carbonate (603 mg, 5.69 mmol), dimethoxyethane (10 mL), and water (3 mL) for 15 min. After this time, the solution was treated with dichlorobis(triphenylphosphine)palladium(II) (121 mg, 0.17 mmol), and the resulting reaction mixture was heated at 90° C. for 2 d. The reaction was then poured into water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 40/60 hexanes/ethyl acetate) afforded 5-(3-methoxy-phenyl)-pyrazin-2-ylamine (218 mg, 63%) as a light yellow solid: mp 113.2–115.5° C.; EI-HRMS m/e calcd for C11H11N3O (M+) 201.0902, found 201.0905.

Workup

customthe resulting reaction mixture
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-015e031f217847f9a20a6d1e301bb2e7
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

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