Process for the preparation of pyrimidine derivatives

Details Process for the preparation of pyrimidine derivatives Process for the preparation of pyrimidine derivatives

1986-05-02

1987-09-08

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544313, C07D23960, C07D23956

Patent

active

046925244

ABSTRACT:
The present invention relates to a process for the preparation of 2-mercapto-4,6-bis-fluoroalkoxypyrimidines of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl and each of T.sub.1 and T.sub.2 independently of the other is hydrogen or a --CHX.sub.1 X.sub.2 group, wherein each of X.sub.1 and X.sub.2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine.
In accordance with this process, 2-mercapto-4-halo-6-hydroxy-pyrimidines of the formula ##STR2## wherein R.sub.1 is as defined above and Y is chlorine or bromine, are reacted with chlorodifluoromethane or a 1,1-difluoroalkene of the formula ##STR3## wherein each of the X.sub.1 and X.sub.2 independently of the other is trifluoromethyl, fluorine, chlorine or bromine, in an inert solvent and in the presence of a strong base, to give a 2-mercapto-4-halo-6-fluoro-alkoxypyrimidine of the formula ##STR4## wherein R.sub.1, Y and T.sub.1 are as defined above, said 2-mercapto-4-halo-6-fluoroalkoxypyrimidine is converted by subsequent reaction with an alkali metal nitrite or an alkaline earth metal nitrite into a 2-mercapto-4-hydroxy-6-fluoroalkoxypyrimidine of the formula ##STR5## wherein R.sub.1 and T.sub.1 are as defined above, and then said 2-mercapto-4-hydroxy-6-fluoroalkoxypyrimidine is converted by reaction with chlorodifluoromethane or a 1,1-difluoroalkene of the above formula into a 2-mercapto-4,6-bix-fluoroalkoxypyrimidine of the above formula.
The 2-mercapto-4,6-bis-fluoroalkoxypyrimidines of the above formula are intermediates for the preparation of herbicidally effective sulfonylureas.

REFERENCES:
patent: 4478635 (1984-10-01), Meyer et al.
patent: 4545811 (1985-10-01), Meyer et al.

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