Patent ID: 6087498
Filing Date: 2000-07-11
Classification: C07D

Abstract:
A process for the preparation of an unsymmetrical 4,6-bis(aryloxy)pyrimidine compound having the structural formula ##STR24## wherein R and R.sub.8 are each independently hydrogen or halogen;R.sub.1 and R.sub.7 are each independently hydrogen, halogen, cyano, nitro, alkyl, trifluoromethyl, pentafluoroethyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, alkoxyalkyl, haloalkoxyalkyl or alkoxycarbonyl;R.sub.2 and R.sub.3 are each independently hydrogen, halogen, alkyl, trifluoromethyl, pentafluoroethyl, haloalkoxy, haloalkenyl, haloalkynyl, haloalkoxyalkyl, alkoxycarbonyl, haloalkoxycarbonyl, haloalkylsulfinyl, haloalkylsulfonyl, nitro or cyano;R.sub.3 and R.sub.5 are each independently hydrogen, halogen, alkyl or alkoxy; andR.sub.4 is hydrogen, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl or phenyl;provided that at least one of R.sub.2 and R.sub.6 is other than hydrogen, and that the aryloxy groups are not the same; which comprises reacting a 4,6-dihalopyrimidine compound having the structural formula ##STR25## wherein R.sub.4 is as described above and X is Cl, Br or I with one molar equivalent or less of a first phenol compound having the structural formula ##STR26## wherein R, R.sub.1, R.sub.2 and R.sub.3 are as described above and a first base in the presence of a first solvent to form a 4-halo-6-(aryloxy)pyrimidine compound having the structural formula ##STR27## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and X are as described above, reacting the 4-halo-6-(aryloxy)pyrimidine compound with at least about one molar equivalent of a C.sub.1 -C.sub.4 trialkylamine, a 5- to 6-membered saturated or 5- to 14-membered unsaturated heterocyclic amine optionally substituted with one to three C.sub.1 -C.sub.4 alkyl groups or C.sub.1 -C.sub.4 alkoxy groups in the presence of a second solvent to form an ammonium halide compound having the structural formula ##STR28## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and X are as described above, Q.sup.+ is ##STR29## R.sub.9, R.sub.10 and R.sub.11 are each independently C.sub.1 -C.sub.4 alkyl, and when taken together, R.sub.9 and R.sub.10 may form a 5- or 6-membered ring in which R.sub.9 R.sub.10 is represented by the structure: --(CH.sub.2).sub.n --, optionally interrupted by O, S or NR.sub.14, where n is an integer of 3, 4 or 5, provided R.sub.11 is C.sub.1 -C.sub.4 alkyl;Z is O, S or NR.sub.14,R.sub.12 and R.sub.13 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and when taken together, R.sub.12 and R.sub.13 may form a 5- or 6-membered saturated or unsaturated ring optionally interrupted by O, S or NR.sub.14 and optionally substituted with one to three C.sub.1 -C.sub.4 alkyl groups or C.sub.1 -C.sub.4 alkoxy groups; andR.sub.14 is C.sub.1 -C.sub.4 alkyl; andreacting the ammonium halide compound with at least about one molar equivalent of a second phenol compound having the structural formula ##STR30## wherein R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as described above and a second base in the presence of a third solvent.