The transmission input shaft and the main shaft with sliding gears for shifting are in line with each other, but are two divided shafts. The fourth and fifth sliding gear has teeth that lock on teeth on the input shaft that are used to lock the shafts together for 5th speed. Teeth could be worn on input shaft, sliding gear or both. Also there is a bearing on the front of main shaft that pilots in input shaft. If its bad the shafts may not line up correct. Problem could be with shifting fork also. Tractors that came on steel used a fifth gear lock out screw. If you got it in gear once and it grindes also, I don't think the lock out is the problem. Sugjest removing the belt pulley gear box or cover to see what teeth look like. Also if shift fork is moving sliding gear forward as it should and for movement or play in or between main shaft and input shaft.
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