Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | HCID 58553813 | HCID 58553813 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66706054 | HCID 66706054 | 56.2% |
Reaction Steps
Process 1: 4′-{[4-butyl-1-(5-hydroxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (27 mg, 0.060 mmol), cyclohexanol (12 mg, 0.120 mmol) and triphenylphosphine (32 mg, 0.122 mmol) were dried for 3 hrs in vacuo, purged with argon, added 1,4-dioxane (1 mL) and diethyl azodicarboxylic acid (2.2 mol/L toluene solution, 70 μL, 0.154 mmol), and then stirred at 80° C. for 3 hrs. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (chloroform:methanol=10:1) to obtain 4′-{{4-butyl-1-[5-(cyclohexyloxy)pyrimidin-2-yl]-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl}methyl}biphenyl-2-carbonitrile (18 mg, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08664226B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-0962ae74779b4b3c8dd70d71cee8951b |
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| Source note | uspto-grants-2014_03 |
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