Is it obligatory to take all possible measures to wake up for prayer, or are some of them sufficient? And is what was mentioned considered an intentional act to miss the prayer?

Some jurists have gone to the extent of stating the obligation of taking measures that aid in waking up for prayer for one who sleeps before its time, and it suffices for this to take whatever measures would lead to the strong presumption of waking up. There is no deliberate neglect of prayer in what the questioner mentioned, as long as he prayed it within its time, but he might incur sin according to those who hold the view that congregational prayer in the mosque is obligatory.