Reaktionsgleichung
ClCl.[C:3]([C:7]1[O:8][C:9]2[C:15]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])=[CH:14][CH:13]=[C:12]([Cl:29])[C:10]=2[N:11]=1)([CH3:6])([CH3:5])[CH3:4].[Cl:30]N(Cl)C(OCC)=O>>[C:3]([C:7]1[O:8][C:9]2[C:15]([N:16]3[C:21](=[O:22])[C:20]([Cl:30])=[C:19]([C:23]([F:25])([F:24])[F:26])[N:18]([CH3:27])[C:17]3=[O:28])=[CH:14][CH:13]=[C:12]([Cl:29])[C:10]=2[N:11]=1)([CH3:6])([CH3:4])[CH3:5]Komponenten
Versuchsvorschrift
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.
Aufarbeitung
- additionAt this point additional substituents may be optionally added to the pyrimidinedione ring
Quellen und Nachweise
- ORD-Eintrag
- ord-0b9f7007d6ea4bd488e2f4bd33ceaf15
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05753595
Verknüpfte Notizen
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