Help: iTunes freezing when I try to transfer purchases from iPad 2.

iTunes freezes when I try to transfer purchases from my iPad 2 to my laptop (MS Vista). It starts to transfer purchases but eventually results in iTunes not responding or my device timing out.  I've tried Disk Cleanup/Defrag and uninstall/re-install of iTunes in the correct sequence. Can anyone please help me?

How is your iPod configured to sync music? In other words, what options and configurations do you have enabled from under your iPod's Summary and Music tabs in iTunes? 
Maybe have a look at this article as well to verify your iPod is set up for syncing music.
iTunes: Syncing media content to iOS devices and iPod
B-rock

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