Cannot transwer new purchased music to ipod on new computer

We have a new computer that we cannot sync our new music purchased today to our ipod. We installed and syncd itunes 2 months ago when we got the computer, but I think this is the first time we have tried to purchase items on it. I say 'we' as this is my mom and dads issue.
They originally shared an apple ID. Apple ID 1 was linked to the ipod. Then they needed their own IDs so apple ID2 was created and the IPod was synced to it as that is the account inwhich new content would be purchased. Apple ID1 stayed the same. The new music we bought was on AppleID2. All music shows in previously purchased. It also shows under library/music. We cannot get the newly purchased music onto the IPod. We hit sync and it does not update the new music. I can not drag and drop it on the ipod or in the playlist which it is intended for. I deleted the music and downloaded it again and its still the same issue. i signed on to apple ID1 and still could not move the content on to the ipod.
IPod touch generation model MC086LL ios 4.2.1
I do not know what Itunes they are using but I assume its up to date on a 2 month old computer that didnt ask to be update upon load up.
Any help would be appreciated. Any questions feel free to ask.

Post in the iPod forum.

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Cannot transwer new purchased music to ipod on new computer

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