US 6,982,331 B2
Synthesis of chlorinated pyrimidines
Timothy J. Doyle, Elmsford, N.Y. (US); Alan H. Benke, Bucks, Ala. (US); Peter K. Wehrenberg, Bucks, Ala. (US); Louie A. Nady, Daphne, Ala. (US); and Gilbert Rodriguez, Bucks, Ala. (US)
Assigned to Syngenta Crop Protection, Inc., Greensboro, N.C. (US)
Filed on Jun. 27, 2003, as Appl. No. 10/608,968.
Application 10/608968 is a continuation in part of application No. 09/876964, filed on Aug. 06, 2001, granted, now 6,608,199.
Prior Publication US 2004/0054181 A1, Mar. 18, 2004
Int. Cl. C07D 409/00 (2006.01); C07D 239/02 (2006.01)
U.S. Cl. 544—240 32 Claims
 
1. A method of synthesizing 4,6-dichloropyrimidine, 5-substituted-4,6-dichloropyrimidines, 4-chloro-6-hydroxypyrimidine, or 5-substituted-4-chloro-6-hydroxypyrimidines, said method comprising reacting a first imidoyl chloride compound represented by the formula:
OG Complex Work Unit Drawing
wherein R2 is hydrogen, C1-4 alkoxycarbonyl, C1-4alkoxysulfinyl, trimethylsilyl or a group —C(OH)′R″ wherein R′ and R″ are independently hydrogen, C1-4alkyl or phenyl, and a second imidoyl chloride compound which has two alpha hydrogens represented by the formula:
OG Complex Work Unit Drawing
wherein R1 is selected from hydrogen and a C1-C12 hydrocarbyl group, with phosgene, diphosgene, triphosgene or oxalyl chloride.