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Music Purchased in iTunes not Syncing to iPhone

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I've never had an issue before. Running OS X 10.6.8, and latest version of iTunes, have an iPhone 5.
Bought some music a week ago, and it's there in my purchased section of iTunes, plays through AppleTV etc, but it's greyed out when I look at the music on the iPhone in iTunes and isn't on the phone itself. I've synced the phone, tried the drag and drop etc, but nothing has worked.
Anyone have any thoughts?

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