| 2,6-Dichloropurine |
| CAS 5451-40-1 |
| EINECS 226-681-6 |
| Molecular Weight = 189.00 |
| Molecular Formula = C5H2Cl2N4 |
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| Specification | |
| Description | White or almost-white crystalline powder |
| Identification | IR is concordant with standard |
| Loss on drying | Not greater than 0.5% w/w |
| Residue on ignition | Not greater than 0.5% w/w |
| Related substances by HPLC | Total impurities maximum 2.0% |
| Purity by HPLC | Minimum 98.0% |
| 2,6-Dichloropurine is a key intermediate for the synthesis of purine derivatives1. It has different reactivities at its three variable positions, C2, C6, and N9, which makes it possible to achieve regioselectivity under appropriate conditions. Typically the 6-chloro group can be replaced with a primary amine or aniline by refluxing in butanol for several hours. Next the N9-position can be alkylated by treatment with potassium carbonate in DMSO followed by the addition of an alkyl halide. The most difficult reaction is the displacement of the C2 position which is the most unreactive site. Examples of biologically active purines in the literature include olomoucine2, roscovitine3, purvalanol A4, myoseverin5, purmorphamine6, reversine7 and diminutol8. |
| 1 QSAR Comb. Sci. 2004, 23, 245-260 |
| 2 Eur. J. Biochem. 1994, 224, 771-786 II |
| 3 US Patent 6,316,456 |
| 4 a) Science 1998, 281, 533-538; b) Chem. Biol. 1999, 6, 361-375 |
| 5 a) Nat. Biotechnol. 2000, 18, 304-309; b) J. Med. Chem. 2001, 44, 4497-4500 |
| 6 J. Am. Chem. Soc. 2002, 124, 14520-14521 |
| 7 J. Am. Chem. Soc. 2004, 126, 410-411 |
| 8 Chem. Biol. 2004, 11, 135-146 |
| For more information or to
discuss your needs contact Dr Will Dehany Tel: +44 1642 591764 Fax: +44 1642 576455 e-mail inters@kemprotec.com. |
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Last updated 10th January 2005