Tris(pyrazolyl)methanes (tpm) are tripodal ligands that form complexes with a variety of metals. Depending on the exact nature of the tpm ligand, octahedral Fe(II) complexes can be either high-spin, low-spin, or display spin crossover behavior. There are numerous examples of tpm ligands being derived from pyrazoles substituted at the 3–position, 4-position, and both the 3– and 5–positions of the pyrazole. We now report that by carefully controlling reaction conditions, lithiation followed by methylation of the three pyrazoles was achieved exclusively at the 5-positions of tris(pyrazolyl)methane leading to the new compound, tris(5-methylpyrazolyl)methane (Scheme 1). The results were quite sensitive to the reaction conditions, with the outcome depending on temperature, solvent, and concentration. Deuteration studies using NMR and GC-MS determined that the tetra-lithiated species is an intermediate. The doubly-charged Fe(II) complex of this new ligand was synthesized and its structure determined with a variety of anions at different temperatures by x-ray crystallography. With large triphenylcyanoborate anions, the Fe(II) complex is low–spin and diamagnetic in the solid state. However, the tetrafluoroborate salt of the complex displays spin crossover behavior with a transition temperature near room temperature (300 K).