Methyl iodide → ethyl 7-(2,2,2-trifluoro-N-methylacetamido)thieno[2,3-b]pyrazine-6-carboxylate

HRID 1184820Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[C:3]([NH:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][N:13]=2)[S:8][C:7]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:4].[C:22](=O)([O-])[O-].[K+].[K+].IC.[NH4+].[Cl-]>CC(C)=O>[F:21][C:2]([F:20])([F:1])[C:3]([N:5]([C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][N:13]=2)[S:8][C:7]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:22])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 7-(2,2,2-trifluoroacetamido)thieno[2,3-b]pyrazine-6-carboxylate 10 (9.22 g, 28.9 mmol) and potassium carbonate (7.98 g, 57.8 mmol) in acetone (140 mL) was added iodomethane (3.60 mL, 57.8 mmol). The reaction was stirred at 50° C. for 1 h. NH4Cl solution(aq) was added and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated to give crude ethyl 7-(2,2,2-trifluoro-N-methylacetamido)thieno[2,3-b]pyrazine-6-carboxylate 11 (9.1 g, 95%). (m/z)=334 (M+H)+.

Workup

extractionextracted with EtOAc
washOrganic layer was washed with brine
customdried
customevaporated

Sources & evidence

ORD record: ord-2e180b294530489a9b166fa05a5e9989
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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