5-Amino-4,6-dichloropyrimidine Chemical Properties

Melting point:

145-148 °C (lit.)

Boiling point:

270.44°C (rough estimate)

Density 

1.6662 (rough estimate)

refractive index 

1.6300 (estimate)

storage temp. 

2-8°C

solubility 

slightly soluble

pka

-3.01±0.26(Predicted)

form 

Crystals or Powder

color 

Yellow-brown

Water Solubility 

slightly soluble

Sensitive 

Moisture Sensitive

BRN 

126885

InChIKey

NIGDWBHWHVHOAD-UHFFFAOYSA-N

CAS DataBase Reference

5413-85-4(CAS DataBase Reference)

NIST Chemistry Reference

5-Amino-4,6-dichloropyrimidine(5413-85-4)

EPA Substance Registry System

5-Pyrimidinamine, 4,6-dichloro- (5413-85-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

F 

10-21

TSCA 

Yes

HS Code 

29335995

MSDS

• Language:English Provider:5-Amino-4,6-dichloropyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Amino-4,6-dichloropyrimidine Usage And Synthesis

Chemical Properties

Yellowish-brown crystals or powder

Uses

An intermediate in the production of many biological inhibitors.

Uses

5-Amino-4,6-dichloropyrimidine was used in the synthesis of:

• oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides
• conformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]octane nucleosides
• N(7)-substituted purines
• chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine
• 9-alkyl-6-substituted-purine analogs, potent anticonvulsant agents
• pyrimido-oxazepines in a three-step process with microwave heating at 150°C

Synthesis

GENERAL METHODS: 10% Pd/C catalyst (0.05 g) was added to a solution of 4,6-dichloro-5-nitropyrimidine (4.48 mmol) in ethyl acetate (EA, 20 mL) in a Parr hydrogenation reactor. Subsequently, the air in the reactor was replaced with nitrogen three times and the hydrogenation reaction was carried out at room temperature and at atmospheric pressure. Upon completion of the reaction, the reaction solution was filtered through a diatomaceous earth filter to remove the Pd/C catalyst, and the filtrate was concentrated to give the target product 4,6-dichloro-5-aminopyrimidine [46].

References

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 1, p. 54 - 58
[2] Tetrahedron, 1988, vol. 44, # 19, p. 6207 - 6216
[3] European Journal of Medicinal Chemistry, 2017, vol. 140, p. 212 - 228
[4] Synlett, 2010, # 20, p. 3019 - 3022
[5] Synthetic Communications, 2007, vol. 37, # 16, p. 2777 - 2786

5-Amino-4,6-dichloropyrimidine(5413-85-4)Related Product Information

• EC 2.6.1.2
• Glucosamine
• 4,6-Diaminopyrimidine
• Glycine
• 6-Aminocaproic acid
• Dichloroethane
• 3-Aminophenol
• ALTRENOGEST
• 4,6-Dichloro-5-fluoropyrimidine
• 4,6-Dichloropyrimidine
• Aminopyrine
• Acetaminophen
• Tris(hydroxymethyl)aminomethane
• 2-AMINO-4,6-DICHLOROPYRIMIDINE 95+%,2-AMINO-4,6-DICHLOROPYRIMIDINE 97+%,2-AMINO-4,6-DICHLOROPYRIMIDINE, TECH. 95%,2-AMINO-4,6-DICHLOROPYRIMIDINE
• 2,5-Diamino-4,6-dichloropyrimidine
• 2,4,6-TRICHLORO-5-NITROPYRIMIDINE
• 5-Amino-4,6-dichloro-2-methylpyrimidine
• N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide