ITunes doesn't allow me to put music in my iPhone 5

Hi. I have realized, that my iTunes doesn't introduce the music I select into my iPhone5. Kind of weird. If I choose just a few songs (5,10) they go in. But if I select a vast amount of them (400+) they just stay with this sign and sometimes with grey color or sometimes and unselectable, or also sometimes just with this sing but selectable. (With selectable I mean I can use it and play it)
I have tried everything. First I thought it was a mess with the enough space, but it isn't. I restart counters but doesn't work. I've updated iTunes, and iPhone (7.1.1) but neither is.
Help me please

Hi. I wonder what do you mean when you say "home button"?
What I understood is that you think i have a Mac computer? I have Windows 7
Or correct me if i'm wrong of course!
And anyway thank you!

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