SIDDALL Tomas Lajman (US),СИДДАЛЛ Томас Лайман (US),ROT Dzhoshua Dzhon (US),РОТ Джошуа Джон (US),SIDDALL Tomas Lajman,СИДДАЛЛ Томас Лайман,ROT Dzhoshua Dzhon,РОТ Джошуа Джон
申请号：
RU2014131389
公开号：
RU0002626957C2
申请日:
2012.12.28
申请国别(地区):
RU
年份:
2017
代理人:
摘要：
FIELD: chemistry.SUBSTANCE: invention relates to novel 2.6-dihalo-5-alkoxy-4-substituted pyrimidines of formula (I) and 2.6-dihalo-5-alkoxy-4-Pyrimidine carboxaldehydes formula (II), which can be used as intermediates for herbicides with a broad spectrum of activity in combating weeds. Describes these compounds as well as processes for their preparation and use thereof. In the compound of formula (I) X1 is halogen； R1 is selected from the group consisting of vinyl, alkenyl, and furyl； and Q represents a C1-C2 alkoxy. In the compound of formula II X1 is halo； and Q represents a C1-C2 alkoxy. The invention also relates to a process for the preparation of 2.6-dihalo-5-alkoxy-4-substituted-pyrimidine derivative of formula (I), wherein the substituent in position 4 of the pyrimidine ring is selected from the group consisting of vinyl, alkenyl, aryl and furyl. The process comprises reacting a 2.6-dihalo-5-alkoxy-pyrimidine with an organometallic reagent of a halide to form 2.6-dihalo-5-alkoxy-4-substituted-3-(metal-halogen or metal)-pyrimidine and oxidizing the resulting 2.6-dihalo-5-alkoxy-4-substituted-3-(metal-halogen or metal)-pyrimidine to form 2.6-dihalo-5-alkoxy-4-substituted-pyrimidine compound of formula (I). As the organometallic reagent is preferably used Grignard reagent such as vinyl magnesium bromide. In can also be used as the organometallic reagent is an organolithium reagent. For the oxidation of 2.6-dihalo-5-alkoxy-4-substituted-3-(metal-halogen or metal)-pyrimidine using 2.3-dichloro-5.6-dicyano-p-benzoquinone. A compound of formula (I), obtained above, wherein R1 is vinyl, can be converted to a compound (II) by oxidation with an oxidizing agent such as ozone. The resultant 2.6-dihalo-5-alkoxy-pyrimidin-carbaldehyde of formula (II) can be treated with bromine in an alcohol to obtain alkyl-2.6-dihalogeno-5-alkoxy-pyrimidin-4-carboxylate, and then treated with an amine to form alkyl-6-amino-2-halo-5-alkoxy-pyrimidin-4-carboxylate. Alternatively, the com
