HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromopyrimidine → 4-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromopyrimidine | HCID 78345 | — |
| Reactant | tert-Butyl 4-ethynylpiperidine-1-carboxylate | HCID 15550481 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | 4-Pyrimidin-2-ylethynyl-piperidine-1-carboxylic acid tert-butyl ester | HCID 66939877 | 8% |
Reaction Steps
To a suspension of 2-bromopyrimidine (175 mg, 1.1 mmols), dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmols) and CuI (10 mg, 0.05 mmols) was added a solution of 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester (209 mg, 1 mmol). The mixture was stirred overnight, filtered through Celite, concentrated. The residue was partitioned between ethyl acetate and water, organic layer was isolated, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate in hexanes (1:1) to give un-reacted 2-bromopyrimidine (130 mg), then the title compound (23 mg). LCMS m/e (288, M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546404B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-e45d7b86119f4a91afdadc37a01a965d |
| Source note | uspto-grants-2013_10 |