FIG. 1.
Preparation of pyridine (A) and pyrimidine (B) compounds (numbers in boldface refer to the various compounds). (A) Reaction a, lithium diisopropylamide, THF, and (R1R2)PhCHO; reaction b, NaH, PhCH2Br and DMF; reaction c, NaH, diethyl carbamoylchloride, and THF; reaction d, NaN3, DMF, and water; reaction e, 2-mercaptoethanol, K2CO3, and DMF; reaction f, chiral-phase preparative high-pressure liquid chromatography. (B) Reaction a, nBuLi, THF, diethylether, and R1R2PhCHO; reaction b, NaH, PhCH2Br, and DMF; reaction c, nBuLi, THF, diethylether; and 2-fluoro-6-trifluoromethylbenzaldehyde; reaction d, NaH, PhCH2Br, and THF.