Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (4-Cyano-3-fluorophenyl)boronic acid | HCID 2783130 | — |
| Reactant | HCID 118483118 | HCID 118483118 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 118483133 | HCID 118483133 | 71% |
Reaction Steps
A mixture of [1-(4-chloro-1-ethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (210 mg, 0.59 mmol) in CH3CN (10 mL), 3-fluoro-4-cyanophenylboronic acid (126 mg, 0.77 mmol), Pd(PPh)4 (14 mg, 0.012 mmol) and 0.4 M Na2CO3 (4.5 mL, 1.77 mmol) was stirred at 90° C. overnight under N2 atmosphere. The organic was concentrated in vacuo, and the aqueous extracted with DCM (2×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica chromatography (1:2, EA:PE) to give 185 mg (64%) of the title compound as a yellow solid. [M+H] Calc'd for C23H28FN5O3, 442. Found, 442.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09255097B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-53286e3e7774493e8e23c902dca3e0a9 |
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| Source note | uspto-grants-2016_02 |
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