Dimethyl Sulfoxide → Methyl 3-(4-(pyridin-2-ylamino)phenoxy)pyrazine-2-carboxylate

HRID 473749Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[C:17]([C:22]([O:24][CH3:25])=[O:23])=[N:18][CH:19]=[CH:20][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[N:18][CH:19]=[CH:20][N:21]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 350 mL sealable tubed was added 4-(pyridin-2-ylamino)phenol (5.16 g, 27.7 mmol), methyl 3-chloropyrazine-2-carboxylate (4.78 g, 27.7 mmol), and cesium carbonate (9.93 g, 30.5 mmol) with DMSO. The tube was sealed and heated to 100° C. for three days. After cooling to temperature, the reaction was diluted with water and extracted with ethyl acetate. The combined, dark brown organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The brown residue was adsorbed onto silica under high vacuum and flash purified on (0.5 to 10% MeOH/DCM), affording the product as a pale tan solid (7.44 g, 23.1 mmol, 83%). MS (ESI, pos. ion) m/z: 323.0 (M+1).

Workup

customThe tube was sealed
temperatureAfter cooling to temperature
extractionextracted with ethyl acetate
dry with materialThe combined, dark brown organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified on (0.5 to 10% MeOH/DCM)

Sources & evidence

ORD record: ord-34ade0f23620424dae5b3ac3869d3174
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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