2-(Tributylstannyl)pyrimidine Chemical Properties

Boiling point:

381.2±25.0 °C(Predicted)

Density 

1.164 g/mL at 25 °C

refractive index 

n20/D1.512

Flash point:

>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

Safety Information

Hazard Codes 

Xi,T,N

Risk Statements 

21-25-36/38-48/23/25-50/53

Safety Statements 

36/37/39-45-60-61-35

RIDADR 

UN 2788 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT, TOXIC, KEEP COLD

HS Code 

29339900

2-(Tributylstannyl)pyrimidine Usage And Synthesis

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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