Business class fare sale to MAD in the spring. But I want to visit Portugal.

So I'm looking at an SFO-YYZ-MAD outbound, which appears to be purchasable as a UA ticket according to GF.

Then I'd take a separate flight from MAD-TP.

YYZ-MAD on AC740 is scheduled to arrive in MAD at 11:20 AM and the TP flight I'm looking at departs at 1:35 PM.

Seems tight but if they check my bags through to LIS on two different tickets, I'm hoping this is possible. The next MAD-LIS direct flight on TP would be 15:30.