Chlorine → 3-(2-t-butyl-4-chlorobenzoxazol-7-yl)-1-methyl-5-chloro-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

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Reaction Steps

At this point additional substituents may be optionally added to the pyrimidinedione ring. For example, a chlorine moiety was added to the 3-(2-t-butyl-4-chlorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione molecule (I) by treating it with N,N-dichlorourethane under acidic conditions, affording 3-(2-t-butyl-4-chlorobenzoxazol-7-yl)-1-methyl-5-chloro-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (III). In addition, the 3-[2-(substituted-methoxyalkyl)-substituted-benzoxazol-7-yl]-1-alkyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (I), for example 3-[2-(1-methoxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione, can be hydrogenated under basic conditions, yielding the targeted 3-[2-(substituted-hydroxyalkyl)-substituted-benzoxazol-7-yl)-1-alkyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (IV), for example 3-[2-(1-hydroxy-1-methylethyl)-4-chloro-6-fluorobenzoxazol-7-yl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione. Examples 3 and 15 provide the detailed procedures for these methods.

Provenance & Evidence