Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Fluoropyridine--hydrogen chloride (1/1) | HCID 24820326 | — |
| Reactant | HCID 89662144 | HCID 89662144 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71612144 | HCID 71612144 | 25% |
Reaction Steps
16.5 mg of 2-[5-cyclopropyl-1-(4-cyclopropyl-2,6-difluorobenzyl)-4-methyl-1H-pyrazol-3-yl]-5-methoxypyrimidin-4-amine 1-17-3 (0.040 mmol, 1.0 eq.) and 16.1 mg 4-Fluoropyridine hydrochlorid (0.120 mmol, 3.0 eq.) were suspended in 0.19 mL dry DMF under a nitrogen atmosphere. 19.2 mg of sodium hydride (60% purity) were added and stirred at 90° C. for 2 h. Then the mixture was partitioned between half water and ethyl acetate. The aqueous layer was washed with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to obtain 5.7 mg (0.01 mmol, 20%) of the analytical pure target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09260412B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-104f61a0bd8942b6a16c7f8c1b940334 |
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| Source note | uspto-grants-2016_02 |
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