2,4-Dichloro-5-aminopyrimidine Chemical Properties

Melting point:

108-112?C

Boiling point:

290.7±20.0 °C(Predicted)

Density 

1.606±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO, Methanol

form 

Solid

pka

-1.55±0.29(Predicted)

color 

Brown

InChI

InChI=1S/C4H3Cl2N3/c5-3-2(7)1-8-4(6)9-3/h1H,7H2

InChIKey

RINHVELYMZLXIW-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(N)C(Cl)=N1

CAS DataBase Reference

5177-27-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39-24/25

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29335990

2,4-Dichloro-5-aminopyrimidine Usage And Synthesis

Chemical Properties

Brown Solid

Uses

A pyrimidinamine derivative as Plk1 inhibitors

Synthesis

General procedure for the synthesis of 5-amino-2,4-dichloropyrimidine from 2,4-dichloro-5-nitropyrimidine: 2,4-dichloro-5-nitropyrimidine (1.0 eq.) and iron powder (6.0 eq.) were formulated in acetic acid to form a non-homogeneous reaction system at a concentration of 0.4 M, and the reaction was carried out for 14 hours at room temperature with vigorous stirring. Upon completion of the reaction, the reaction mixture was thermally filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was washed with methanol (MeOH) and the volatile solvent was subsequently evaporated under reduced pressure. The resulting residue was dissolved in ethyl acetate (EtOAc) and washed sequentially with saturated sodium carbonate (Na2CO3) solution and saturated sodium chloride (NaCl) solution to remove acidic impurities and salts. The organic phase was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the target product 5-amino-2,4-dichloropyrimidine in 80% yield. The product was analyzed by liquid chromatography-mass spectrometry (LCMS), showing a molecular ion peak (MH+) of 157.0 and a retention time (Rt) of 1.85 min.

References

[1] Patent: US2011/195980, 2011, A1. Location in patent: Page/Page column 17
[2] Patent: WO2011/106168, 2011, A1. Location in patent: Page/Page column 83; 84; 101; 102
[3] Journal of the Chemical Society, 1951, p. 1565,1568
[4] Journal of the Chemical Society, 1953, p. 1646
[5] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 352,354

2,4-Dichloro-5-aminopyrimidine(5177-27-5)Related Product Information

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• 1,2-Dichloro-4-(chloromethyl)benzene
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• Glycine
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• 3-Aminophenol
• ALTRENOGEST
• EC 2.6.1.2
• 2,4-Dichloropyrimidine
• Acetaminophen
• 5-Amino-2-chloropyrimidine
• Tris(hydroxymethyl)aminomethane
• 2,4-Dichloro-6-methyl-5-nitropyrimidine
• 2,4-DICHLORO-5-AMINO-6-METHYLPYRIMIDINE
• 2,4,6-TRICHLORO-5-NITROPYRIMIDINE
• 2,6-Dichloro-4-aminopyrimidine
• 2,4-Dichloro-5-nitropyrimidine
• 2,4-Dichloro-5-(1H-pyrazol-1-yl)pyrimidine