I managed to get through on chat tonight, but that didn't go as well as I hoped. I mentioned that Alaska wasn't star alliance a few times, and that award space was abundant on themselves as well as other partners for the destination I was planning. The rep couldn't find any space, and I even tried to have the rep look between Portland and Seattle, two hubs that always have good availability. The rep couldn't find any award space there either over multiple months. After enough times of me suggesting they weren't Star alliance and that they may be on a different search tool, the agent ended the chat with me.

One thing I found, is that the flight I am wanting doesn't seem to be bookable on their site, Seattle to Fairbanks, which is a non-stop. The Singapore tool didn't allow Fairbanks as an entry.

As for making this booking, I suppose the points I have in Singapore I expected to expire a couple of years ago, but they got extended enough that I was hoping I could find a use for them. I don't plan to make any transfers to Singapore in the future based on this, but may try a couple more times before calling it quits. If I can't make the booking, then I suppose the points were meant to be lost either way.