Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 57785853 | HCID 57785853 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57785814 | HCID 57785814 | 82% |
Reaction Steps
To a solution of [9-chloro-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]acetonitrile (176.0 mg, 0.478 mmol) in tetrahydrofuran (4.5 mL) was added ethyl iodide (57.3 μL, 0.717 mmol) and potassium tert-butoxide (75.8 mg, 0.574 mmol) at 0° C., The reaction mixture was stirred at 0° C. for 1 hr under nitrogen atmosphere. The mixture was quenched with aqueous saturated ammonium chloride and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-60% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless powder (154.3 mg, 0.390 mmol, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785460B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-0c51903078ad47b4a69307a3102126df |
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| Source note | uspto-grants-2014_07 |
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