last played info does not sync from phone to mac

I have a rather large music collection (I had to pare it down to fit under the 25,000 song iTunes Match limit). I have tracks that have never played since I imported them into iTunes. To listen to them, I set up a smart playlist of songs whose play count is zero. Easy enough, and it does indeed show songs I've never played in iTunes. What's more, the playlist works on both my Mac and my iPhone. And it updates on the iPhone - I can see the number of tracks decline as songs are played. However, when I return to my Mac those songs played on the iPhone still show up as never played. I can wait for days and they still don't sync with what I've done on the iPhone. (Playing songs on my AppleTV doesn't seem to ever update the last-played date or the play count, but that's another matter.)

It used to be that I could manually sync iTunes Match and get things back in sync between the Mac and the iPhone, but at some point the "sync iTunes Match" command disappeared from the iTunes menus. Is there any way to get my Mac to recognize what has been played on my iPhone?