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.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid After Melting

pka

8.68±0.10(Predicted)

color 

Clear yellow

Water Solubility 

almost transparency

Sensitive 

Hygroscopic

BRN 

151178

InChIKey

MRBFGEHILMYPTF-UHFFFAOYSA-N

CAS DataBase Reference

20980-22-7(CAS DataBase Reference)

Safety Information

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

MSDS

• Language:English Provider:1-(2-Pyrimidyl)piperazine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-(1-Piperazinyl)pyrimidine Usage And Synthesis

Chemical Properties

clear yellow liquid after melting

Uses

2-(1-Piperazinyl)pyrimidine (Buspirone EP Impurity A) is the major metabolite of Tandospirone (T006430).

Uses

The major metabolite of Tandospirone.

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 K?CO? (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 Na?SO? 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(20980-22-7)Related Product Information

• 2-Ethylhexyl ferulate
• Piperazine
• Piperacillin
• 1-Methylpiperazine
• N-Aminoethylpiperazine
• Homopiperazine
• 2-Chloropyrimidine
• Dihydrochloride
• BUSPIRONE (D8)
• 3,3-Tetramethyleneglutarimide
• Buspirone EP Impurity F
• 8-(pyrimidin-2-yl)-5,8-diazaspiro[4.5]decan-5-ium chloride
• Buspirone Impurity 1 (Lactone of 6-Hydroxy Buspirone)
• 8-(4-Chlorobutyl)-8-azaspiro[4.5]decane-7,9-dione
• Buspirone EP Impurity H
• Buspirone Impurity 2
• Buspirone N-Oxide
• Buspirone impurity 3