Cant add PDF files, itunes doesnt show me the option to add the files

Sometimes itunes dosnt show me the option to add files under the Aplications Menu.
I have already installed ADOBE READER, and when trying to add PDF files, itunes dosnt show me the applications to add files.
Below you will find the options that sometimes dissapear.

This may help - http://www.simplehelp.net/2010/06/22/how-to-add-pdf-files-to-read-in-ibooks-on-y our-ipad-ipod-touch-or-iphone/.  It is for the older version of iTunes, however it should give you some good guidance.

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