2-CHLORO-5-NITROPYRIMIDIN-4-AMINE Chemical Properties

Melting point:

221-226 °C

Boiling point:

446.0±25.0 °C(Predicted)

Density 

1.712±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

-1.22±0.10(Predicted)

form 

Solid

Appearance

Light yellow to yellow Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C4H3ClN4O2/c5-4-7-1-2(9(10)11)3(6)8-4/h1H,(H2,6,7,8)

InChIKey

RZGOEIWDMVQJBQ-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C(N)=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37-36

WGK Germany 

3

HS Code 

29335990

2-CHLORO-5-NITROPYRIMIDIN-4-AMINE Usage And Synthesis

Chemical Properties

Yellow to brown solid

Uses

It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

Synthesis

General procedure for the synthesis of 2-chloro-4-amino-5-nitropyrimidines from 2,4-dichloro-5-nitropyrimidines: a solution of 2,4-dichloro-5-nitropyrimidines (30 g, 154.36 mmol) was slowly added dropwise to a solution of 2,4-dichloro-5-nitropyrimidines (30 g, 154.36 mmol) in dichloromethane (DCM) with ammonia (NH3-H2O, aqueous solution, 24 mL) and N,N-diisopropylethylamine ( DIPEA, 37.2 mL) to a mixed solution of DCM (400 mL). The reaction mixture was stirred continuously at 0 °C for 1 h, followed by filtration. The collected solid was dried to give the target product 2-chloro-4-amino-5-nitropyrimidine (25 g, 92.6% yield) as a yellow solid. It was analyzed by liquid chromatography-mass spectrometry (LCMS, ESI) and m/z: 175.0 ([M+H]+) was measured.

References

[1] Patent: US2017/313683, 2017, A1. Location in patent: Paragraph 0541-0542
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10685 - 10699
[3] Patent: EP2578584, 2013, A1. Location in patent: Paragraph 0071; 0072
[4] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 2, p. 321 - 328
[5] Patent: EP3284743, 2018, A1. Location in patent: Paragraph 0135

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