What I did my son is 2.5 y old is I took the second nap away n I put her s nap from 3-5:30 and we come up for bed around 11 n he falls asleep w n an hour
I always try and keep my daughter entertained and not let her have a nap. If she does it's about an hour one then she's up. I'd make sure he takes an early one so he's not sleeping late and before bed a warm bath and full tummy