Abstract
showed similar trends (entries 3-6). Thecorresponding 5-chloro derivatives 2c and 2d were obtainedin good yields (82-90%) and dichlorohydrin derivatives 3cand 3d were obtained in good yields (83-84%). 5-Substitut-ed uracil derivatives, 1e and 1f, produced the correspondingchlorohydrins 3e and 3f (entries 7 and 8). The relatively lowyield of 3f might be due to the presence of a large 5-bromosubstituent in 1f. The 5-bromination and dibromohydrinformation of 1b were carried out with 48% aqueous HBrsolution in DMF (entries 9 and 10). The yield of 5-bromo-1,3-dimethyluracil (2e) was reasonable (62%) while theyield of dibromohydrin 3g was low (41%) due to a similarsteric reason as in the case of 3f. When we used aqueousHCl (37%) instead of dry HCl gas, the yield of 2b decreasedto 51% (rt, 2 h, 1.5 equiv of KHSO
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