8-CHLOROADENINE

8-Chloroadenine (1) To a solution of adenosine (2.67 g, 10 mmol) in DMA/HCl (0.5M, 45 mL) was added m-chloroperoxybenzoic acid (MCPBA, 3.22 g, 16 mmol 87%) and stirred at room temperature for 2.5 h. An additional portion of MCPBA (0.9 g, 5 mmol) was added and stirring continued for another 1 h. Toluene (50 mL) was added to the reaction mixture and the solvents evaporated at 60 C. under vacuo to dryness. The residue was dissolved in water (50 mL) and extracted with ether (3*50 mL). The pH of the aqueous phase was adjusted to 5 with 2N NaOH and then diluted with EtOH (100 mL). The solution was stored in the refrigerator overnight. The light yellow solid that separated was collected, washed with cold EtOH (2*25 mL) and dried to give 1.44 g (85.2%) of 1: mp 305-310 C. (dec.) [Lit. mp>300 C. (dec.)]: IR (KBr): 630 (C-C1), 3100-3300 (NH2) cm-1: UV: lambdamax (pH 1) 262 nm (epsilon 8, 700): lambdamax (pH 7) 268 nm (epsilon 7, 900): lambdamax (pH 11) 269 nm (epsilon 8, 300): 1 H NMR (Me2 SO-d6): delta 7.48 (br s, 2, NH2), 8.10 (s, 1, C2 H) and 13.60 (br s, 1, N9 H).

Molecular Weight:169.57
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:169.0155228
Monoisotopic Mass:169.0155228
Topological Polar Surface Area:80.5
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes