HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1984236Generated: November 2, 2026
Triethylamine → 4-(2,2-Dimethyl-propylamino)-5-{3-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-1-ynyl}-pyrimidine-2-carbonitrile
https://huagongshe.com/reaction/1984236
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 | 1-Methyl4-(4-prop-2-ynyl-phenyl)-piperazine | HCID 57714126 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2,2-Dimethyl-propylamino)-5-{3-[4-(4-methyl-piperazin-1-yl)-phenyl]-prop-1-ynyl}-pyrimidine-2-carbonitrile | HCID 44450271 | 25% |
Reaction Steps
To a solution of 1-methyl-4-(4-prop-2-ynyl-phenyl)-piperazine (0.75 mmol) and 5-bromo-4-(2,2-dimethyl-propylamino)-pyrimidine-2-carbonitrile (0.5 mmol) in THF (7 ml), triethylamine (1.5 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.025 mmol) and copper (I) iodide (0.05 mmol) are added. The reaction mixture is heated at 60° C. ca. for 3 h. 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 sodium sulfate and concentrated under vacuum to give crude product which is purified by reverse phase HPLC. Yield: 25%. Rf=0.5 (MeOH:CH2Cl2=5:95)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07544688B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-6f7e1074d73f41fa895178e9b5ac46a8 |
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| Source note | uspto-grants-2009_06 |
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