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| | 2-(1-Piperazinyl)pyrimidine Basic information |
| | 2-(1-Piperazinyl)pyrimidine Chemical Properties |
| Melting point | 32-34°C | | Boiling point | 277 °C (lit.) | | density | 1.158 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.587(lit.) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 8.68±0.10(Predicted) | | form | Liquid After Melting | | color | Clear yellow | | Water Solubility | almost transparency | | Sensitive | Hygroscopic | | BRN | 151178 | | InChI | 1S/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2 | | InChIKey | MRBFGEHILMYPTF-UHFFFAOYSA-N | | SMILES | C1CN(CCN1)c2ncccn2 | | CAS DataBase Reference | 20980-22-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-24/25 | | WGK Germany | 3 | | RTECS | UV9702000 | | TSCA | Yes | | HazardClass | 8 | | HS Code | 29335990 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-(1-Piperazinyl)pyrimidine Usage And Synthesis |
| Chemical Properties | clear yellow liquid after melting | | Uses | The major metabolite of Tandospirone. | | Uses | 2-(1-Piperazinyl)pyrimidine (Buspirone EP Impurity A) is the major metabolite of Tandospirone (T006430). | | Definition | ChEBI: 1-(2-Pyrimidyl)piperazine is a N-arylpiperazine. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 18, p. 1484, 1953 DOI: 10.1021/jo50017a004 | | General Description | 1-(2-Pyrimidyl)piperazine is a piperazine-based derivative. It is a metabolite of buspirone. | | Synthesis | Generic method: 2-chloro-4,6-disubstituted pyrimidines (17) were prepared by reaction of the diazonium salt of 4,6-disubstituted pyrimidin-2-amine (16) with concentrated hydrochloric acid and ZnCl[35]. Compound 18 was synthesized with reference to the method of literature [32] with modifications. To a stirred solution of piperazine (45 mmol) and KCO (16.5 mmol) in water (20 mL) was added 2-chloro-4,6-disubstituted pyrimidine (17) (18 mmol) in batches at 50-65 °C. The reaction mixture was stirred at 60-65 °C for 1 hour and subsequently cooled to 35 °C. The solid by-product 1,4-bispyrimidinylpiperazine was removed by filtration, the filtrate was extracted three times with chloroform, the organic phase was dried with NaSO and concentrated under reduced pressure to give compound 18, which could be used in the subsequent reaction without further purification.18a: yellow oil, 88% yield. | | References | [1] Chinese Journal of Chemistry, 2015, vol. 33, # 10, p. 1124 - 1134
[2] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
[3] Organic Letters, 2016, vol. 18, # 20, p. 5272 - 5275
[4] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11357 - 11360
[5] Patent: CN107216318, 2017, A. Location in patent: Paragraph 0021; 0024; 0027 |
| | 2-(1-Piperazinyl)pyrimidine Preparation Products And Raw materials |
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