Scheme 1.

Synthesis of 2-pyridinyl-6-methylpyrimidines. Reagents & Conditions: (i) MeONa/MeOH, rt; (ii) NH₄Cl/MeOH, 65-74% yields for two steps; (iii) H₃C-COCH(X)CO₂Et (6), MeONa/MeOH, 45-53% yields; (iv) POCl₃, reflux, 65-72% yields; (v) PhCH₂CH₂NH₂, K₂CO₃/MeOH, 65 °C, 85-92% yield; (vi) (R)-H₂NCH₂CH(Ph)NHBoc (10), Et₃N, THF, 82-95% yields; (vii) CF₃CO₂H/CH₂Cl₂, then aqueous NaHCO₃, 81-86% yields. Yield for 9a, 9b, and 9c were 56%, 62%, and 49% over three steps, respectively.