Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate | HCID 73828 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | Stannane, tributyl(1-ethoxyethenyl)- | HCID 619414 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86689172 | HCID 86689172 | 64.1% |
Reaction Steps
A mixture of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester [1458-18-0] (600 mg, 2.62 mmol), lithium chloride (389 mg, 9.17 mmol), Pd(PPh3)2Cl2 (184 mg, 0.262 mmol) and tributyl-(1-ethoxy-vinyl)-stannane [97674-02-7] (1.6 ml, 4.50 mmol) in DMF (27 ml) under argon was heated at 80° C. bath temperature for 3 h and 50 min. Saturated aq. NH4Cl was added and the mixture was extracted with MTBE (3×). The combined organic layers were washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 7:3) to provide the title compound as yellow solid (433 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09163011B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-15a36c48b6a6446cb0b5d09784d395aa |
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| Source note | uspto-grants-2015_10 |
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