318 Magnum first fire...timing?

I attempted to fire the 318 magnum for the first time on yesterday. Had a few setbacks. When I finally got around to starting it, it was dark. After it didn't start I didn't fool around too much to troubleshoot or make adjustments, but here's how it went.

I primed the oil pump first. The guy that rebuilt the engine said he primed it previously but that was about 8 months ago so I figured I needed to. I spun the crank by hand until it read TDC and the rotor was pointed toward the number #1 cylinder.
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Then I removed the distributor.
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I took a picture of how the oil pump drive gear was oriented prior to removal. I inserted the 5/16 hex rod and spun with the drill. I was reading just under 80 psi. I replaced the oil pump drive gear in the same orientation as it was prior to removal. Replaced the distributor with the rotor pointed in the same direction, towards #1 cylinder.

When I attempted to start the engine, I cranked it 4 times with no fire. On the 5th crank there was a LARGE backfire that sounded like a shotgun blast.

I think there may be one of two issues.
#1 I am using MSD wires and a flame thrower coil. The rubber boot on the coil wire does not go onto the flame thrower coil easily. It seems as though the outer housing is too thick for the rubber boot. So maybe the coil wire isn't' fully connecting and I'm not getting spark.
OR
#2 My rotor is off 180 degrees. In my quick research I have read that a large backfire can mean it is firing on the exhaust stroke rather than the compression stroke.

To fix the 180 degrees out issue, with the crank spun to TDC as done previously, would I lift up the distributor out to where the rotor spins freely, spin it 180 degrees and then drop the distributor back down?

BUT WAIT THERE's MORE.

I noticed my freeze plugs were leaking coolant. After the large backfire we started packing up for the night. As I'm cleaning all the tools up I checked under the car and saw a couple wet spots. Come to find out, my freeze plugs are leaking. Just a steady slow drip.
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Can anyone tell if that plug is seated correctly? Why would they be leaking already!?! Is there a fix for this with the engine in the car. I don't particularly want to run stop leak in a freshly rebuilt engine.

Needless to say, it was a frustrating day. Any advice is appreciated.

If you'd like the watch the video of the backfire I uploaded it. Get a laugh out of my Dad jumping out of his shoes.



Here's a picture of what we're workin with.
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Yep, pull the distributor and turn it 180 then drop it back in.
Also know that it is just too damn east to get plug wires 5 and 7 reversed. (Chk your firing order)

A person can put the engine on TDC but have it on the exhaust stroke instead of the intake stroke.
If for example you pull the #1 plug and and turn the motor over until blows a piece of paper towel out of the plug hole, then bring it up to TDC and you can be sure it’s on the compression stroke.

Your distributor drive gear is right the way it is in your pictures.
It really doesn’t matter where it is oriented anyway, as long as your distributor rotor is pointing at the #1 terminal on the cap with the engine at TDC on the compression stroke.