3-Amino-5-(2-methoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester → 3-Amino-5-(2-methoxy-ethyl)-pyrazine-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([CH:12]=[CH:13][O:14][CH3:15])=[CH:7][N:6]=1)=[O:4]>CCO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([CH2:12][CH2:13][O:14][CH3:15])=[CH:7][N:6]=1)=[O:4]Participants
4
Procedure
A solution of 3-amino-5-(2-methoxy-vinyl)-pyrazine-2-carboxylic acid methyl ester (260 mg, 1.24 mmol) and Pd/C 10% (50 mg) in EtOH (10 ml) was stirred at rt and under an atmosphere of hydrogen for 17 h. To complete the reaction, more Pd/C 10% (84 mg) was added and the reaction was stirred under an atmosphere of hydrogen for 37 h. The suspension was filtered off and washed with EtOH and then residual solution was evaporated. The residue was purified by chromatography on silica gel (DCM to DCM/MeOH 9:1) to provide the title compound as yellow solid (147 mg).
Workup
- additionwas added
- filtrationThe suspension was filtered off
- washwashed with EtOH
- customresidual solution was evaporated
- customThe residue was purified by chromatography on silica gel (DCM to DCM/MeOH 9:1)
Sources & evidence
- ORD record
- ord-0381abb2503a4e06b54eaf8a21e1eb86
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163011B2
Reaction notes
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