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| | 6-Chloro-2-fluoropurine Basic information |
| | 6-Chloro-2-fluoropurine 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 | | 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) |
| | 6-Chloro-2-fluoropurine 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 | 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 Preparation Products And Raw materials |
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