We have found there is a dependence between the size and content of the template library used, and the domain in which it is applied. We found that syntheses of compounds originating from combinatorial libraries could be predicted using the most frequently occurring reactions. In contrast, compounds originating from libraries requiring more complex syntheses, required an expanded template set for their successful prediction. Further work is required to make use of the broad selection of reactions available to improve the variety and complexity of routes suggested. Further investigations into the template extraction process are also required to determine their descriptive limits and how this translates into route prediction.