Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate → Methyl 5-amino-2,6-dichloropyrimidine-4-carboxylate
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([N+:12]([O-])=O)=[C:4]([Cl:15])[N:3]=1>C(O)(=O)C.[Fe]>[NH2:12][C:5]1[C:6]([C:8]([O:10][CH3:11])=[O:9])=[N:7][C:2]([Cl:1])=[N:3][C:4]=1[Cl:15]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A mixture of methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (5 gm, 20 mmol) and powdered iron (5 gm) in acetic acid (40 mL) was heated at 60° C. There was a vigorous exotherm within 5 minutes and the reaction was allowed to cool to room temperature. The acetic acid was removed and the residue was suspended in a mixture of water and diethyl ether. This was filtered and the solid was washed with diethyl ether. The organic phase was separated, washed with saturated aqueous NaHCO3 solution (twice) and brine, dried over sodium sulfate, and the solvent removed to leave methyl 5-amino-2,6-dichloropyrimidine-4-carboxylate (2.1 gm) as a yellow brown solid. MS (ESI) m/z 222.0 and 224.0 (M+H). 1H NMR (CDCl3) δ ppm 6.20 (2H, br. s.), 3.99 (3H, s).
Workup
- customwithin 5 minutes
- temperatureto cool to room temperature
- customThe acetic acid was removed
- additionthe residue was suspended in a mixture of water and diethyl ether
- filtrationThis was filtered
- washthe solid was washed with diethyl ether
- customThe organic phase was separated
- washwashed with saturated aqueous NaHCO3 solution (twice) and brine
- dry with materialdried over sodium sulfate
- customthe solvent removed
Sources & evidence
- ORD record
- ord-24528fcfd91d463ca998fd2f3d6920c0
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815840B2
Reaction notes
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