ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 6-Chloro-2-fluoropurine

6-Chloro-2-fluoropurine

Product Name6-Chloro-2-fluoropurine
CAS1651-29-2
MFC5H2ClFN4
MW172.55
EINECS634-083-5
MOL File1651-29-2.mol

Chemical Properties

Melting point	162-163°C
Boiling point	221.8±50.0 °C(Predicted)
Density	1.98±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml
form	powder to crystal
pka	4.88±0.20(Predicted)
color	White to Light yellow to Green
ex/em	λex 451, 435 nm; λem 503, 477 nm
InChI	InChI=1S/C5H2ClFN4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)
InChIKey	UNRIYCIDCQDGQE-UHFFFAOYSA-N
SMILES	N1C2C(=NC(F)=NC=2Cl)NC=1
CAS DataBase Reference	1651-29-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-41-37/38-22-37/39-26
Safety Statements	26-36/37/39-39
WGK Germany	3
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

Description

6-Chloro-2-fluoropurine is a heterocyclic building block. It has been used in the synthesis of purine nucleosides that inhibit cyclin-dependent kinases (CDKs) in vitro. 6-Chloro-2-fluoropurine has also been used in the synthesis of purine nucleosides that are active against HIV-1 and hepatitis B virus (HBV) in vitro.

Chemical Properties

Beige solid

Uses

6-Chloro-2-fluoropurine is used as a reagent in the synthesis of several organic compounds including that of 2''-Fluoro-3''-Hydroxymethyl-5''-deoxythreosyl phosphonic acid nucleoside analogues which may potentially act as antiviral agents. It is also used in the synthesis of 2'',5'',5''-trifluoro-3''-hydroxy-apiosyl nucleoside phosphonic acid analogues which may possess potent anti-HCMV properties.

Synthesis

10310-21-1

1651-29-2

General procedure for the synthesis of 6-chloro-2-fluoro-9H-purine from 2-amino-6-chloropurine: 0.3 M NaNO2 aqueous solution (200 mL, 60 mmol) was slowly added dropwise to a vigorously stirred suspension of 2-amino-6-chloro-9H-purine (6.0 g, 35.4 mmol) at -15 °C. Subsequently, 120 mL of 48% HBF4 aqueous solution (0.92 mol) was added over 75 min. The reaction mixture was stirred at room temperature and kept in a light yellow reaction solution state for 20 min. After cooling again to -15 °C, it was neutralized with 50% NaOH aqueous solution to pH=6.0. The water was removed by vacuum and the orange solid obtained was purified by silica gel column chromatography (eluent ratio 90:10 dichloromethane to methanol, Rf value 0.50). 6-Chloro-2-fluoro-9H-purine was finally obtained as a white solid (3.0 g, 49.1% yield).

References

[1] Journal of Organic Chemistry, 1992, vol. 57, # 14, p. 3887 - 3894
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1746 - 1767
[3] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1161 - 1164
[4] Patent: US2002/68721, 2002, A1
[5] Patent: WO2004/16612, 2004, A2. Location in patent: Page 54

6-Chloro-2-fluoropurine

Chemical Properties

Safety Information

Usage And Synthesis

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