Guanidine Hydrochloride → Methyl 2-aminopyrimidine-5-carboxylate
Reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[CH3:6][O:7][CH:8]([O:18]C)[CH:9]([CH:13](OC)OC)[C:10]([O-])=O>CN(C)C=O>[CH3:6][O:7][C:8]([C:9]1[CH:10]=[N:4][C:3]([NH2:5])=[N:2][CH:13]=1)=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a stirred solution of 4.30 g guanidine hydrochloride in 50.00 g dimethyl formamide, 10.00 g 3,3-dimethoxy-2-dimethoxymethyl-propionate were added. The resulting clear solution was heated to 100° C. for 2 hours and to 140° C. for an additional 20 hours. After cooling to 60° C., the solvent was completely removed in vacuo and the resulting light brown residue thoroughly extracted with boiling tetrahydrofurane. After distilling off the majority of the solvent, the crystalline product was isolated by suction filtration and subsequent drying in vacuo. A total of 4.34 g (63% of theory based on 3,3-dimethoxy-2-dimethoxymethyl-propionate) of methyl-2-amino-pyrimidine-5-carboxylate could be isolated in this way. Identification of the product was based on 1H-NMR-, 13C- and IR-spectra.
Workup
- temperatureAfter cooling to 60° C.
- customthe solvent was completely removed in vacuo
- extractionthe resulting light brown residue thoroughly extracted with boiling tetrahydrofurane
- distillationAfter distilling off the majority of the solvent
- customthe crystalline product was isolated by suction filtration
- customsubsequent drying in vacuo
- customA total of 4.34 g (63% of theory based on 3,3-dimethoxy-2-dimethoxymethyl-propionate) of methyl-2-amino-pyrimidine-5-carboxylate could be isolated in this way
Sources & evidence
- ORD record
- ord-8af47238b83840219e6b95241b5902d8
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06153752
Reaction notes
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