Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Di-tert-butyl azodicarboxylate | HCID 97268 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | HCID 59484885 | HCID 59484885 | — |
| Reactant | HCID 67439965 | HCID 67439965 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59484963 | HCID 59484963 | — |
Reaction Steps
197 mg of 3-cyanophenylpyridazinone (1.00 mmol) is suspended in a mixture of 5 ml of abs. THF and 1 ml of abs. DMF in an N2-flushed apparatus with CaCl2 protection, 301 mg of 1-{3-[5-(3-dimethylaminopropoxy)-pyrimidin-2-yl]phenyl}ethanol (1.00 mmol) and 500 mg of polymer-bound triphenylphosphine (1.5 mmol) are added, the mixture is stirred at RT for 30 min, 345 mg of di-tert-butyl azodicarboxylate (1.5 mmol) are subsequently added with ice/H2O cooling and stirring, and the mixture is stirred at RT for a further 2 h. For work-up, the reaction mixture is diluted with 10 ml of methanol, and the polymer is removed by filtration. The residue is washed with dichloromethane, and the combined filtrate is evaporated to dryness in a rotary evaporator and purified by chromatography (silica gel: DCM+0-30% of MeOHF), giving “A298”, m.p. 105-7° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09284300B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-dc76e7ff6a9d48ebba6d7e4d88de63d6 |
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| Source note | uspto-grants-2016_03 |
|---|