5-BROMOPYRIMIDIN-4-AMINE Chemical Properties

Melting point:

207-211℃

Boiling point:

282.2±20.0 °C(Predicted)

Density 

1.844±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3?+-.0.10(Predicted)

form 

Powder

color 

Pale brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C4H4BrN3/c5-3-1-7-2-8-4(3)6/h1-2H,(H2,6,7,8)

InChIKey

IIFAONYUCDAVGA-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933599590

5-BROMOPYRIMIDIN-4-AMINE Usage And Synthesis

Uses

It is an inhibitor of thymidine phosphorylase, an enzyme known to be over-expressed in several tumor types and to play a role in metastasis.

Synthesis

The synthesis of 4-amino-5-bromopyrimidine was carried out using the compound (CAS: 163133-86-6) as starting material according to a modified scheme of the literature method 7: 4-aminopyrimidine (1.00 g, 10.5 mmol, 1.0 eq.) was dissolved in water (20 mL) with CaCO3 (263 mg, 2.63 mmol, 0.25 eq.) followed by slow addition of bromine (Br2, 1.06 mL, 20.5 mmol, 2.0 eq.). The reaction mixture was stirred at 60 °C for 45 min, then cooled to room temperature and poured into dichloromethane (CH2Cl2, 20 mL) for layering. After separation of the organic layer, the aqueous layer was further extracted with dichloromethane (2 x 20 mL). All organic layers were combined and stored temporarily. The aqueous layer was adjusted to pH 9-10 with 20% aqueous K2CO3 to induce precipitation of the product. The precipitate was collected by filtration and dried to afford the target product 4-amino-5-bromopyrimidine (1.08 g, 6.22 mmol, 59% yield) as a light tan solid.

References

[1] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 81 - 86
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 12, p. 3654 - 3661
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5247 - 5250
[5] European Journal of Medicinal Chemistry, 2008, vol. 43, # 6, p. 1248 - 1260

5-BROMOPYRIMIDIN-4-AMINE(1439-10-7)Related Product Information

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