4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE Chemical Properties

Melting point:

252 °C (decomp)

Boiling point:

336.7±37.0 °C(Predicted)

Density 

1.565

Flash point:

157℃

storage temp. 

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

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

powder to crystal

pka

2.39±0.10(Predicted)

color 

White to Amber to Dark green

λmax

305nm(lit.)

Stability:

Hygroscopic

InChI

InChI=1S/C4H5ClN4/c5-3-2(6)4(7)9-1-8-3/h1H,6H2,(H2,7,8,9)

InChIKey

VNSFICAUILKARD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4316-98-7

EPA Substance Registry System

4,5-Pyrimidinediamine, 6-chloro- (4316-98-7)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29335990

4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

4-Amino-6-chloropyrimidin-5-ylamine is a chlorinated diaminopyrimidine used in the preparation of various bioactive choloropurine derivatives.

Synthesis

Step 1: 4,6-Dichloropyrimidin-5-amine (1.64 g, 10 mmol) was suspended in 5 mL of concentrated hydrochloric acid. The suspension was transferred to a sealed tube, ammonia solution was added and the reaction was stirred at 100 °C overnight. Upon completion of the reaction, the solid product was collected by filtration and dried under vacuum to afford the target compound 6-chloropyrimidine-4,5-diamine as a yellow solid (1.2 g, 83% yield).LC-MS analysis showed m/z 145 ([M+H]+).

References

[1] Patent: WO2006/46023, 2006, A1. Location in patent: Page/Page column 115-116
[2] Patent: WO2008/75110, 2008, A1. Location in patent: Page/Page column 116
[3] Patent: WO2007/125315, 2007, A2. Location in patent: Page/Page column 115
[4] Patent: WO2007/125325, 2007, A1. Location in patent: Page/Page column 92-93
[5] Organic Process Research and Development, 2011, vol. 15, # 4, p. 841 - 854

4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE(4316-98-7)Related Product Information

• 4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE
• 4-CHLORO-6-HYDRAZINO-PYRIMIDIN-5-YLAMINE
• 6-CHLORO-5-NITROPYRIMIDIN-4-AMINE
• 4-Chloro-2,6-diaminopyrimidine
• 2,6-Diamino-4-chloropyrimidine 1-oxide
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• IFLAB-BB F2124-0139
• IFLAB-BB F2124-0138
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• 6-CHLORO-N4,N4-DIMETHYL-PYRIMIDINE-4,5-DIAMINE
• IFLAB-BB F2124-0125
• 4-CHLORO-6-(4-METHYL-1-PIPERAZINYL)-5-NITROPYRIMIDINE
• N4-METHYL-6-CHLORO-5-NITROPYRIMIDIN-4-AMINE
• 4-CHLORO-6-PIPERIDIN-1-YL-PYRIMIDIN-5-YLAMINE
• N4-benzyl-6-chloropyrimidine-4,5-diamine
• 4-CHLORO-5-NITRO-6-(1-PYRROLIDINYL)PYRIMIDINE
• N-benzyl-6-chloro-5-nitro-4-pyrimidinamine