ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Chloropyrimidine 2-Amino-4-chloropyrimidine

2-Amino-4-chloropyrimidine

Product Name2-Amino-4-chloropyrimidine
CAS3993-78-0
MFC4H4ClN3
MW129.55
EINECS
MOL File3993-78-0.mol

Chemical Properties

Melting point	155-160 °C (dec.)
Boiling point	314.6±34.0 °C(Predicted)
Density	1.437±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Soluble in dimethyl sulfoxide.
pka	3.55±0.10(Predicted)
form	Solid
color	White
InChI	InChI=1S/C4H4ClN3/c5-3-1-2-7-4(6)8-3/h1-2H,(H2,6,7,8)
InChIKey	DBGFGNCFYUNXLD-UHFFFAOYSA-N
SMILES	C1(N)=NC=CC(Cl)=N1
CAS DataBase Reference	3993-78-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-41-37/38-22
Safety Statements	26-36/37/39-36/39-60
WGK Germany	3
Hazard Note	Irritant
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Amino-4-chloropyrimidine is a substrate used in a palladium-catalyzed cyanation with zinc(II) cyanide. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Synthesis

3934-20-1

7461-50-9

3993-78-0

2,4-Dichloropyrimidine (1.0 g, 6.7 mmol) was used as starting material and 28% w/v aqueous ammonium hydroxide solution (20 mL) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure. The obtained residue was dried and subsequently purified by fast column chromatography (FCC) with the eluent being chloroform solution containing 2-10% ethanol, resulting in the isolation of 2-amino-4-chloropyrimidine and 2-chloro-4-aminopyrimidine. Product yields: 200 mg of 2-amino-4-chloropyrimidine in 23% yield and 600 mg of 2-chloro-4-aminopyrimidine in 69% yield.

Purification Methods

It has also been purified by sublimation in a vacuum and recrystrallisation from H2O. [Hilbert & Johnson J Am Chem Soc 52 1155 1930, Beilstein 24 H 80, 25 III/IV 2117.]

References

[1] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 62
[2] Journal of the American Chemical Society, 2003, vol. 125, # 33, p. 9970 - 9982
[3] Tetrahedron, 2010, vol. 66, # 6, p. 1280 - 1288
[4] Patent: WO2006/114409, 2006, A1. Location in patent: Page/Page column 18
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 1973 - 1978

2-Amino-4-chloropyrimidine

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