In this work we describe the solvent free synthesis of supramolecular polyurethanes held together by heterocomplementary triple hydrogen bonding. We perform a systematic evaluation on the base catalyzed synthesis of small molecule ureas and carbamates from a range of isocyanates, amines and alcohols in solution and in the solid state using ball milling. These optimized procedures are then shown to be applicable to the synthesis of supramolecular polyurethanes using solvent-free methods.