Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 57929479 | HCID 57929479 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 57929475 | HCID 57929475 | 78.8% |
Reaction Steps
To a mixture of 5-amino-6-bromo-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (50 mg, 0.15 mmol), phenylboronic acid (28 mg, 0.22 mmol), tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) in 0.6 mL toluene and 0.6 mL EtOH was added cesium carbonate (0.17 g, 0.52 mmol). The resulting mixture was heated at 100° C. in a microwave reactor for 30 min. The reaction mixture was cooled, NaHCO3 (sat'd aq) added and the mixture extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×10 mL) and evaporated under reduced pressure. The crude residue was purified by preparative TLC (Hexanes:EtOAc, 2:1) to afford 40 mg of 5-amino-8-cyclobutyl-2-methylsulfanyl-6-phenyl-8H-pyrido[2,3-d]pyrimidin-7-one as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08268840B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-425cbc7c36564a74af853945be834793 |
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| Source note | uspto-grants-2012_09 |
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