Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 5-Bromo-4-(2,2-dimethylpropylamino)pyrimidine-2-carbonitrile | HCID 17968161 | — |
| Reactant | HCID 57714139 | HCID 57714139 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57714143 | HCID 57714143 | 93% |
Reaction Steps
To a solution of 4-benzyl-1-prop-2-ynyl-piperazine-2,6-dione (1.5 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (1 mmol) in DMF (5 ml), triethylamine (3.0 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) and copper (I) iodide (0.2 mmol) are added. The reaction mixture is heated at 85° C. ca. for 1 day. Saturated aqueous solution of ammonium chloride is added to the reaction mixture and then aqueous layer is extracted with two 50 ml portions of AcOEt. The combined extracts are washed with brine, dried over magnesium sulfate and concentrated under vacuum to give crude product, which is purified by silica gel column chromatography. Yield: 93%. Rf=0.3 (AcOEt only)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07544688B2 |
|---|
| Source dataset | uspto-grants-2009_06 |
|---|
| ORD ID | ord-f2f7d3455a93410f91fac00c4d61b2da |
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| Source note | uspto-grants-2009_06 |
|---|
