Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzophenone | HCID 3102 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | 5-Bromopyrimidine | HCID 78344 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 13813644 | HCID 13813644 | 48.4% |
Reaction Steps
A solution of 5-bromopyrimidine (10 g, 0.063 mol) in a mixture of dry THF (150 mL) and hexane (50 mL) was cooled to −100° C. To this cooled solution was added n-BuLi (4 g, 21 mL, 0.062 mol) over a period of 30 min and stirred for another 30 min. A solution of benzophenone (11.5 g, 0.063 mol) in dry THF (50 mL) was added to this at the same temperature over a period of 30 min. The reaction mixture was warmed slowly to RT and allowed to stir another 1 h at RT. The reaction was quenched with cold water (200 mL), ethyl acetate was added and the organic layer was separated. The organic layer was dried, concentrated and the crude product was purified by column chromatography on silica gel (up-to 25% ethyl acetate in pet ether) to give the product (8 g). TLC: Pet. ether/EtOAc, 1:1, Rf=0.3
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07795270B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-8123864c7c204b688da0571921086332 |
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| Source note | uspto-grants-2010_09 |
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