Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (6-Methoxypyridin-3-yl)boronic acid | HCID 2734368 | — |
| Reactant | HCID 178496588 | HCID 178496588 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 178488428 | HCID 178488428 | 41.7% |
Reaction Steps
To a vial containing 2-amino-6-bromo-8-(trans-4-methoxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (75 mg, 0.20 mmol), 2-methoxy-5-pyridineboronic acid (37.5 mg, 0.245 mmol) and cesium carbonate was added PdCl2(dppf)1:1 w/CH2Cl2 followed by 5:1 dimethoxyethane:water (3 mL, degassed by bubbling with argon). The vial was capped and heated in the microwave for 30 minutes at 100° C. The reaction mixture was concentrated and the crude product was purified by flash chromatography eluting with chloroform/methanol (0-5%). The fractions containing the desired product were concentrated and the solids were triturated with methyltertbutyl ether to afford 2-amino-8-(trans-4-methoxycyclohexyl)-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (33 mg, 40%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273755B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-773a59256fd6439ea16288baf0b98aff |
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| Source note | uspto-grants-2012_09 |
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