Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | N-(2-Methylpropyl)piperidine-3-carboxamide--hydrogen chloride (1/1) | HCID 17750377 | — |
| Reactant | Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate | HCID 86665647 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 50996616 | HCID 50996616 | — |
Reaction Steps
A mixture of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.100 g; 0.300 mmol), N-isobutylpiperidine-3-carboxamide hydrochloride (0.198 g; 0.901 mmol) and triethylamine (0.211 mL; 1.50 mmol) in a mixture of tetrahydrofuran (2 mL) and DMF (0.4 mL) was heated at 110° C. in a sealed tube for 18 h. After cooling, the reaction mixture was diluted in a saturated solution of sodium hydrogen carbonate and extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane (with 0.5% of triethyl amine) furnished 0.150 g (quantitative) of the title compound as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08906906B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-9cc8da033b3b4ea1aeaeef3c133ae902 |
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| Source note | uspto-grants-2014_12 |
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