Reduction of 5-(aryl-diazenyl)-4,6-dihalo-pyrimidine

Abstract

Method of synthesizing a compound of formula (I), wherein R1, R2 are, independently, chloro or fluoro, and wherein R3 is H, alkyl, aralkyl or is an alkylether or alkylthioether comprising the steps of firstly reducing a diazeny compound of formula (II) non-catalytically or with a catalytic amount of an homogenous organic, non-metal catalyst to the corresponding hydrazo compound of formula (III) and in a second step catalytically hydrogenating said hydrazo compound in with a heterogeneous Ni-catalyst to the compound of formula (I).

1 - 10 . (canceled) 
     
     
         11 . A compound of formula IV 
       
         
           
           
               
               
           
         
         or of formula V 
       
       
         
           
           
               
               
           
         
         Wherein R1, R2 are, independently, chloro or fluoro, and wherein R3 is H, aralkyl, alkyl or is an alkylether or alkylthioether, the alkyl moiety being linear or branched and preferably being Cl—ClO alkyl, more preferably being C1-C4 alkyl. 
       
     
     
         12 . A compound of formula VI 
       
         
           
           
               
               
           
         
         wherein R3 is H, alkyl, aralkyl or is an alkylether or alkylthioether, the alkyl moiety being linear or branched and preferably being Cl—ClO alkyl, more preferably being C1-C4 alkyl. 
       
     
     
         13 . (canceled) 
     
     
         14 . A compound of formula II 
       
         
           
           
               
               
           
         
         or of formula III 
       
       
         
           
           
               
               
           
         
         wherein R1, R2 are, independently, chloro or fluoro, and wherein R3 is H, aralkyl, alkyl or is an alkylether or alkylthioether, the alkyl moiety being linear or branched and preferably being Cl—ClO alkyl, more preferably being C1-C4 alkyl, and wherein n=1 to 5 and wherein each R4 n , independently, is halogeno or is alkyl or is alkoxy, preferably wherein halogeno is chloro or fluoro and preferably wherein alkyl is C1-C6 alkyl or alkoxy, with the proviso, that at least one R4 n  is halogeno and/or with the proviso that where R3 is a C1-C4 alkylthioether radical, preferably where R3 is S-propylthioether radical, then either is n>2 or R4≠p-alkyl, preferably is R4 n ≠p-methyl, and/or with the proviso, that where R3 is C1-C6 alkyl, preferably that where R3 is methyl, in formula II, more preferably that where R3 is C1-C6 alkyl or is methyl in formula I or II, that then either is n>2 or R4≠p-chloro or o-chloro preferably wherein n=1, more preferably that then R4≠chloro preferably wherein n=1, most preferably that then R4≠o-halogeno, p-halogeno, p,o-dihalogeno or o,o-dihalogeno wherein n=1 or 2. 
       
     
     
         15 . Compound according to  claim 14 , characterized in that n=1 with R4 being chloro or fluoro, preferably R4 being in para- or ortho-position. 
     
     
         16 . Compound according to  claim 11 , characterized in that R1,R2 are chloro. 
     
     
         17 . (canceled) 
     
     
         18 . Compound according to  claim 12 , characterized in that R1,R2 are chloro. 
     
     
         19 . Compound according to  claim 14 , characterized in that R1,R2 are chloro.