4.6- Dichloro-2-phenyl-pyrimidine

Direct-seeded rice does not tolerate pretilachlor in doses required for adequate weed control. The Ciba Geigy AG has discovered and developed a new safening agent, 4,6-dichloro-2-phenyl-pyrimidine (CGA123 407,23), which protects the rice seedling from damage and does not interfere with the herbicidal activity of pretilachlor. 

Isoxazolo[4,5-d]pyrimidine, 7-bromo-5-chloro-X-ray, 6, 618 <72J8X(2)251) Isoxazolo[4,5-d]pyrimidine, 5,7-dichloro-3-phenyl-UV, 6, 620 <67X675)... 

The reaction of 4,6-dichloro-5-aminopyrimidine 396 with phenyl isothiocyanate in the presence of triethylamine afforded directly 7-substituted aminothiazolo[5,4-4]pyrimidines 397 in a modest yield (Equation 61). Better yields... 

Replacement of the two chlorine atoms in 3-phenyl-5,7-dichloro-l,2,3-triazolo[4,5-d]pyrimidine gave 3,5,7-trisubstituted triazolopyrimidine derivatives [84JAP(K)5962595], which showed anticarcinogenic activity against sarcoma tumor cells in mice. Compounds 159 have been used as an-ticarcinogenics [81JAP(K)8131586,81JAP(K)8131587]. 

Pyrimidin 2,6-Dichloro-5-ethoxycar-bonyl-4-phenyl- E9b/2, 120 [C1jC-N = CC12 +... 

Cbz Cp DABCO DBU DDQ (DHQD)2CLB (DHQD)2PYR DMF DME DMPU DMSO Et Fmoc HMPA ia KHMDS LDA LiHMDS Me MEM Ms NaHMDS Ph Piv PMB Pr Py (saltmen)Mn(N) benzyloxy carbonyl p 5 -cyclopentadienyl l,4-diazabicyclo[2.2.2]octane l,8-diazabicyclo[5.4.0]undec-7-ene 2,3 -dichloro-5,6-dicyanobenzoquinone dihydroquinidinyl p-chlorobenzoale (see Chart 1) dihydroquinidinyl pyrimidine (see Chart 1) dimethylformamide dimethoxyethane l,3-dimethyl-3,4,5,6-tetrahydro-2(l//)-pyrimidinone dimethylsulfoxide ethyl 9-fluorenylmethoxy carbonyl hexamethylphosphoric triamide inverse addition potassium hexamethyldisilazide lithium diisopropylamide lithium hexamethyldisilazide methyl (2-methoxy ethoxy )methyl methanesulfonyl sodium hexamethyldisilazide phenyl pivaloyl p -methoxy benzyl propyl pyridine nitrido[A,A/-(l,l,2,2-tetramethyl) bis(salicylideneaminato)]manganese (see Chart 1)... 

This gives the 4-pyrimidone ring, which is converted into the 4,5-dichloro-6-(l-fluoroethyl)pyrimidine by the action of sulfuryl chloride in the presence of dimethylformamide (DMF) [68]. The chlorine on the 4-position of the pyrimidine ring is substituted with the side chain 2-[4-(trifluoromethyl)phenyl]ethylamine through a nucleophilic substitution reaction [63]. The side chain 2-[4-(trifluoro-methoxy)phenyl]ethylamine is prepared by chloromethylation of trifluorome-thoxybenzene followed by displacement of the chlorine atom with cyanide and reduction of the nitrile with Raney nickel [69]. 

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