HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2189325Generated: October 26, 2026
Triethylamine → 4-[2-Chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol
https://huagongshe.com/reaction/2189325
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Butyn-2-ol | HCID 16239 | — |
| Reactant | 5-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amine | HCID 58015891 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-[2-Chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol | HCID 86637349 | 54.4% |
Reaction Steps
To a mixture of (5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (0.44 g, 1.58 mmol), Pd(Ph3P)2Cl2 (0.11 g, 0.16 mmol), and CuI (0.03 g, 0.16 mmol) in DMF (14 mL) is added 3-butyn-2-ol (0.19 mL, 2.37 mmol) and triethylamine (0.44 mL, 3.16 mmol). The reaction mixture is stirred at 55° C. for 16 h, diluted with CH2Cl2, filtered through a pad of Celite, and concentrated in vacuo. Purification by flash chromatography (SiO2, EtOAc/Hexane 1:3) gave 0.23 g of 4-[2-chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol as yellowish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324225B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-4026a3e2b21a4241b3be186b505cb193 |
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| Source note | uspto-grants-2012_12 |
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