HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 716740Generated: October 25, 2026
5-Bromo-2-chloropyrimidine → 2-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine
https://huagongshe.com/reaction/716740
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 5-Bromo-2-chloropyrimidine | HCID 606665 | — |
| Reactant | cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene | HCID 5706773 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine | HCID 86691332 | 32.7% |
Reaction Steps
A mixture of 5-bromo-2-chloropyrimidine (800 mg), CIS-tributyl[2-ethoxyethenyl] tin (1.80 g), PdCl2(PPh3)2 (30 mg), and toluene (10 mL) was stirred under a nitrogen atmosphere at an outside temperature of 100° C. for 4 hours. After cooling, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (SNAP Cartridge KP-NH: 28 g, mobile phase: n-hexane/EtOAc=100/0 to 85/15 (v/v)) to yield 2-chloro-5-[(Z)-2-ethoxyethenyl]pyrimidine (250 mg, colorless solid).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09193695B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-4284070172bf4e90afc238e19ce7eb39 |
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| Source note | uspto-grants-2015_11 |
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