After many attempts, I was able to transfer music to my Tom Tom. You are not able to do it from itunes ( probably blocked by Microsoft). I transferred tunes from Windows Media Player to "My Music" In Media Player, you right click on the album (or song)then click on convert , then select MP3 files and convert the album/songs. Then I was able to transfer the songs to my Tom Tom, by opening Tom Tom Home, clicking on add maps, etc; then clicking on "Music", then dragging the tunes from "My Music" to the Tom Tom Music folder.
Hope that helps