Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | (5-Chloro-2-methylphenyl)boronic acid | HCID 2773336 | — |
| Reactant | HCID 49788132 | HCID 49788132 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 70979645 | HCID 70979645 | 87% |
Reaction Steps
To a solution of ethyl 5-(2-aminopyrimidin-4-yl)-2-bromo-1H-pyrrole-3-carboxylate (prepared according to WO2007/110344, 2.0 g, 6.43 mmol) dissolved in EtOH (20 mL) and toluene (20 mL), LiCl (408 mg, 9.64 mmol), 1 M aq Na2CO3 (17 mmol), 5-chloro-2-methylphenylboronic acid (1.423 g, 8.35 mmol) and Pd(Ph3P)2Cl2 (470 mg, 0.67 mmol) were added and the reaction mixture was heated at 100° C. for 5 h. After cooling to room temperature, the precipitate was filtered and the filtrate was evaporated under reduced pressure, dissolved in DCM and washed with water. The organic layer was then dried over sodium sulfate and concentrated. The crude material was chromatographed on silica gel (DCM/EtOAc 50/50) to afford the title compound (1.99 g, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912200B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-c1581db90e294fcb9ed002a2958b65dc |
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| Source note | uspto-grants-2014_12 |
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