| Identification | Back Directory | [Name]
2-(Tributylstannyl)pyrimidine | [CAS]
153435-63-3 | [Synonyms]
SKL1126
2-tributyltinpyrMidine
2-(tributyltin) pyrimidine
-(Tributylstannyl)pyrimidine
Tributyl(2-pyrimidyl)stannane
PyriMidine,2-(tributylstannyl)-
2-(Tributylstannanyl)pyrimidine
(Pyrimidin-2-yl)tributylstannane
2-(tri-n-butylstannyl)pyrimidine
Tributyl(pyrimidin-2-yl)stannane
2-(Tributylstannyl)pyrimidine 95%
2-(Tributylstannyl)pyrimidine ,97%
2-(Tributylstannyl)pyrimidine ISO 9001：2015 REACH
(Pyrimidin-2-yl)tributylstannane, 2-(Tributylstannyl)-1,3-diazine | [Molecular Formula]
C16H30N2Sn | [MDL Number]
MFCD01319085 | [MOL File]
153435-63-3.mol | [Molecular Weight]
369.13 |
| Chemical Properties | Back Directory | [Boiling point ]
381.2±25.0 °C(Predicted) | [density ]
1.164 g/mL at 25 °C | [refractive index ]
n20/D1.512 | [Fp ]
>110℃ | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
soluble in Methanol; Ethyl Acetate; Dichloromethane; Chloroform; DMF; DMSO | [form ]
liquid | [pka]
1.42±0.33(Predicted) | [color ]
Colourless | [InChI]
InChI=1S/C4H3N2.3C4H9.Sn/c1-2-5-4-6-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3; | [InChIKey]
WTFFOOAJSDVASL-UHFFFAOYSA-N | [SMILES]
C1([Sn](CCCC)(CCCC)CCCC)=NC=CC=N1 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [Uses]
2-(Tributylstannyl)pyrimidine is an organotin compound used in Stille coupling reaction. This can be used as one of the precursors in the synthesis of 2-aminopyridine oxazolidinones as potent and selective tankyrase (TNKS) inhibitors and the synthesis of canagliflozin, a novel inhibitor for sodium-dependent glucose cotransporter.
It can also be used in the preparation of various (2-pyrimidyl)silanes. | [Synthesis]
Under nitrogen protection, tributyltin hydride (12.5 g) was dissolved in 20 mL of anhydrous tetrahydrofuran in a round bottom flask. With stirring at 0 °C, 2M lithium diisopropylammonium (18.75 g) was slowly added with continuous stirring for 30 min. Subsequently, the reaction system was cooled to -18 °C and 2-chloropyrimidine (4 g, 35 mmol) dissolved in 20 mL of anhydrous tetrahydrofuran was slowly added dropwise. After the dropwise addition, the reaction system was gradually warmed to room temperature and stirring was continued for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of 30 mL of water and extracted with ethyl acetate. The organic phases were combined, concentrated under reduced pressure to remove the solvent, and finally purified by column chromatography to afford 2-(tributyltin)pyrimidine (11.68 g, 90% yield). | [References]
[1] Patent: KR2018/75381, 2018, A. Location in patent: Paragraph 0071; 0072-0074
[2] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 58; 77; 95 |
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