Cut the tar on the outside perimeter of the flashing with a utility knife. Pry the flashing off of the roof with a flat pry bar. Once the flashing is disconnected from the roof, grab the collar around the vent pipe and lift the collar and flashing away from the pipe.
Slide the new drainpipe flashing over the vent pipe until the flat rectangular flashing is flush against the roof. Drive roofing nails through the flashing at each corner and into the roof with a hammer. Drive two more roofing nails into each side of the flashing between the corner nails.
Apply roofing tar to the exposed perimeter of the vent pipe flashing where it meets the roof with a putty knife.
Bend the top of the vent pipe flashing collar over the top of the pipe with a ball peen hammer.