My 2003 IPOD Won't Update with Purchased Music from ITunes

Hi!
My 2003 IPOD won't update with my Itunes purchased music when I sync.
I have reset, restored, updated with the latest versions of IPOD updater as well as Itunes.
Still no purchased music on my IPOD.
Can anyone help me?
2003 IPOD    

Specific songs from the iTunes Music Store don't play
Try deauthorizing and reauthorizing your computer. Repeat the deauthorization and reauthorization process for any other iTunes Music Store accounts for which your computer is authorized.
1.Double-click one of your affected iTunes Music Store songs.
2.Enter your account name and password in the resulting dialog.
3.Click OK.
After you've deauthorized and reauthorized your computer, open iTunes, select your iPod, and choose Update iPod from the File menu. If that doesn't resolve the issue, try restoring your iPod.
After you've restored your iPod, open iTunes, select your iPod, and choose Update iPod from the File menu. If that doesn't resolve the issue, try recreating your iTunes library.
After you've recreated your iTunes library, open iTunes, select your iPod, and choose Update iPod from the File menu.

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