I'm not 100% sure what you are after but here goes
I would approach using interconnects
Create 5 interconnects
1. Default, connects to all interconnects.
2. PRI trunks, allow connection to 4
3. Analog trunks, allow connection to 5
4. Extensions to use PRI trunks, allow connection to 2 and 5
5. Extensions to use analog trunks, allow connection to 3 and 4
You then modify your ars digits dialed to point to a list, that list then points to two routes (one for the PRI trunks and the other for the analog trunks)
Add the new interconnects to your trunks and extensions
With this ext 101 is on interconnect 5 when it tries to make a call it will fail on the PRI trunks and the go out the analog trunks
It may need some fine tuning depending what exactly you are trying the achieve.