Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 68703130 | HCID 68703130 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68708811 | HCID 68708811 | — |
Reaction Steps
To a solution of the crude 4-(2-{5-allyloxycarbonylamino-2-cyano-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester (230 mg) in THF (10 mL) are added trietylamine (1.25 mmol) and Pd(PPh3)4 (catalytic amount) at room temperature under N2 atmosphere. After stirring at the same temperature for 1 h, the reaction mixture is diluted with AcOEt. The organic layer is washed with H2O and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give 4-(2-{5-Amino-2-cyano-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester; 1H-NMR (CDCl3), δ: 0.97-1.07 (2H, m), 1.13-1.28 (4H, m), 1.42-1.88 (25H, m), 2.69 (2H, t), 3.22 (2H, s), 3.31 (2H, t), 4.04-4.16 (2H, m), 4.40 (2H, t), 4.51 (1H, t).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07704996B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-270bec02e9234692ad98c330e4593188 |
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| Source note | uspto-grants-2010_04 |
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