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Hey Vivian,
There is no harm in letting him stay awake for longer than 2 – 21/2 hours just before bedtime and see what happens. Every baby is different so he might be fine having a longer wake window before bedtime.
When your little one wakes from his last nap of the day I recommend you offer him a feed and then offer another feed before bed. This is the only time I recommend you feed them 2 times during a wake window.
Having the final feed at the start of the bedtime routine can be helpful. So for example, your baby’s bedtime routine might start with you feeding him in the living room with the lights on. After the feed, you might go and change his nappy, put his pjs on, put on his sleeping bag, turn off the lights, close the blinds and then sing him a song as you rock him in your arms, then lay him down in the crib awake to fall asleep. The key is to have the feed at the start of the bedtime routine so he doesn’t fall asleep while feeding.
Feeding him closer to bedtime may help to stop those frequent wakings at the start of the night.
I hope that helps!
Emma