Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 2-(3-aminophenyl)acetate | HCID 13042040 | — |
| Reactant | Ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate | HCID 53249641 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86756054 | HCID 86756054 | 95.8% |
Reaction Steps
A mixture of 5 g (21.5 mmol) of ethyl 4-chloro-2-methylthio-pyrimidine-5-carboxylate and 4 g (22.3 mmol) of ethyl 3-aminophenylacetate in 80 ml of 1,4-dioxan was treated with 6 ml (43 mmol) of triethylamine and then heated at 60° C. for 4 hours. The mixture was cooled and evaporated. The residue was partitioned between 120 ml of ethyl acetate and 100 ml of 2M hydrochloric acid. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 7.4 g (92%) of ethyl 4-[3-(ethoxycarbonylmethyl)phenyl]amino-2-methylthiopyrimidine-5-carboxylate as a pale orange colored oil which solidifies slowly to a white solid. [Mass spectrum (ESI) MH+ =376].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06150373 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-76ca81a53c5f40359fad061ad22cb3b0 |
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| Source note | uspto-grants-2000_11 |
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