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Hi Simona,
It sounds like a couple of factors could be contributing to the frequent wake-ups at the start of the night.
The first factor is the timing of his last nap, specifically when it ends. As you noticed, when his nap ended at 6:45 pm, he wasn’t ready for bed at his usual bedtime. This is because he needed more time to build up his sleep pressure. To ensure he is tired enough to fall asleep and stay asleep at bedtime, you may need to cap this nap. If possible, try to cap his last nap of the day to end by 5:30 pm. If that seems too long of a wake window, you could try 6:00 pm and see what happens.
The second factor is the pacifier. It might be causing him to wake up between sleep cycles and making it more challenging to fall back asleep if it falls out. If you have the time and energy, I would recommend gradually fading out the pacifier.
It also sounds like extending his naps after he wakes doesn’t improve his sleep overnight. In fact it seems to be making it worse. So if you’re happy to I recommend you just get him up when he wakes from a nap and start the next wake window. And spend this time helping him learn how to fall asleep on his own in the crib. Once he learns this skill he should naturally start to extend his naps.
I hope this helps!
Emma