Trifluoroacetic acid → HCID 178508569, compound

Participants

Reaction Steps

2-fluoro-8-((7-iodo-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-9H-purin-6-amine (S10-5). S10-4 (0.310 g, 1.03 mmol), NIS (0.301 g, 1.34 mmol), CH3CN (20 mL), TFA (2.34 g, 1.56 mL, 20.5 mmol) was stirred at rt overnight. The mixture was dried under reduced pressure and the residue chromatographed (CH2Cl2:MeOH:AcOH, 120:1:0.5 to 90:1:0.5) to give 0.340 g (77%) of a mixture of S10-5 (m/z 428.2 [M+H]+) along with diiodinated compound (m/z 554.1 [M+H]+). LC-MS shows ratio of S10-5 to diiodinated compound to be 83:17. This mixture was not separated but used further in the following step. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 7.37 (s, 1H), 6.82 (s, 1H), 4.25 (s, 4H), 4.18 (s, 2H); MS (ESI) m/z 428.2 [M+H]+.

Provenance & Evidence