Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diiodomethane | HCID 6346 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | HCID 57785977 | HCID 57785977 | — |
| Reactant | HCID 178418750 | HCID 178418750 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57785868 | HCID 57785868 | 92% |
Reaction Steps
To a stirred solution of 9-chloro-1-(2,4-dichlorophenyl)-6-[1-(ethenyloxy)propyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (246 mg, 0.563 mmol) in dichloromethane (5.6 mL) was added a solution of diethyl zinc in hexane (1.0 M, 2.82 mL, 2.82 mmol) and diiodomethane (454 μL, 5.63 mmol) at 0° C. After 1.5 h, the reaction mixture was diluted with ethyl acetate, quenched with aqueous ammonium chloride, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 0-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a pale yellow solid (233 mg, 0.517 mmol, 92%). Analytically pure material was obtained by recrystallization from ethyl acetate/hexane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08785460B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-7f105e451986418d9d005893d494b049 |
|---|
| Source note | uspto-grants-2014_07 |
|---|