Ethyl (2-amino-6-(2-methoxyethoxy)-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate → Ethyl (2,3-diamino-6-(2-methoxyethoxy)pyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=2)[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([O:33][CH2:34][CH2:35][O:36][CH3:37])[N:3]=1>CCO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([N:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][P:25]([O:27][CH2:28][CH3:29])([O:30][CH2:31][CH3:32])=[O:26])=[CH:22][CH:23]=2)[C:12](=[O:16])[O:13][CH2:14][CH3:15])[CH:5]=[C:4]([O:33][CH2:34][CH2:35][O:36][CH3:37])[N:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of ethyl (2-amino-6-(2-methoxyethoxy)-3-nitropyridin-4-yl)(4-((diethoxyphosphoryl)methyl)benzyl)carbamate (1 equiv.) in EtOH (0.05 M) was added 10% Pd/C (50% equiv. by weight) in a Paar Shaker Flask. The reaction mixture was placed in a Paar Shaker at 55 psi for 4 h. At this point the reaction mixture was passed through a pad of Celite, washing with a 2:1 mixture of CHCl3:MeOH. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was used in the next step without further purification.
Workup
- washwashing with a 2:1 mixture of CHCl3
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- customthe volatiles were removed in vacuo
- customThe resulting residue was used in the next step without further purification
Sources & evidence
- ORD record
- ord-34ca6a394dd84677a0bc6def2e37cbe5
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315530B2
Reaction notes
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