Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | 2-Methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester | HCID 13957268 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178469234 | HCID 178469234 | 51.6% |
Reaction Steps
A solution of 2-methoxy-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester (3.71 g crude) in dimethylformamide (15 ml) was treated with methylamine hydrochloride (1.01 g, 15.0 mmoles) and sodium acetate (1.49 g, 17.0 mmoles). The reaction was allowed to stir at room temperature for 48 hours. It was then diluted with ethyl acetate and filtered. The filtrate was washed with water, sodium bicarbonate, brine and was dried over anhydrous magnesium sulfate. Solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (5-7% ethyl acetate, dichloromethane). The product was crystallized from dichloromethane-isopropyl ether-hexanes to provide the title compound as yellow crystals (1.91 g), melting point 112.5°-114.5° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04689414 |
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| Source dataset | uspto-grants-1987_08 |
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| ORD ID | ord-16733fb8f88e40cebbb31f02556d9601 |
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| Source note | uspto-grants-1987_08 |
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