Pyrimidines fluoro

Pyrimidine, 2-ethyl-1,4,5,6-tetrahydro-synthesis, 3, 108 Pyrimidine, 5-formyl-2-methyl-in thiamin biosynthesis, 1, 99 Pyrimidine, fluoro-syhthesis, 3, 140 Pyrimidine, 2-fluoro-NMR, 3, 63 synthesis, 3, 140 Pyriihidine, 4-fluoro-synthesis, 3, 140 Pyrimidine, 6-fluoro-synthesis, 3, 140 Pyrimidine, fluoroalkyl-synthesis, 3, 77... 

Flucytosine. Flucytosine (17) or 5-fluorocytosine (4-amino-5-fluoro-2-pyrimidone, 5-FC), C H FN O, is a pyrimidine derivative, that is efficient against Candida albicans Cryptococcus neoformans and Torulopsis glabrata. 

Pyrimidin-2-amine, 4-benzyIoxy-6-fluoro-hydrolysis, 3, 92 Pyrimidin-2-amine, 5-bromo-basic pK, 3, 61 Busch reaction, 3, 99 Pyrimidin-2-amine, 4-t-butyl-diazotization, 3, 85... 

Pyrimidine, 4-fluoro-2-isopropyl-synthesis, 3, 140 Pyrimidine, 4-fluoro-2-methoxy-synthesis, 3, 140 Pyrimidine, 4-fluoro-2-methyl-NMR, 3, 63 Pyrimidine, halo-aleoholysis, 3, 100 aminolysis, 3, 99 as antitumour agents, 3, 152 bipyrimidines from, 3, 103 Buseh biaryl synthesis, 3, 103 hydrolysis, 3, 101... 

Pyrimidin-2( 1H) -one, 5-fluoro-1 -methyl-4-methylthio-alcoholysis, 3, 96 Pyrimidin-2(lH)-one, 5-hydroxy-benzoylation, 3, 89... 

Selective fluonnation in polar solvents has proved commercially successful in the synthesis of 5 fluorouracil and its pyrimidine relatives, an extensive subject that will be discussed in another section Selective fluonnation of enolates [47], enols [48], and silyl enol ethers [49] resulted in preparation of a/phn-fluoro ketones, fieto-diketones, heta-ketoesters, and aldehydes The reactions of fluorine with these functionalities is most probably an addition to the ene followed by elimination of fluonde ion or hydrogen fluoride rather than a simple substitution In a similar vein, selective fluonnation of pyridmes to give 2-fluoropyridines was shown to proceed through pyridine difluondes [50]... 

Instead of perchlorates, tnfluoromethanesulfonates (Inflates) can be used They are readily prepared and claimed to be safer than perchlorates [75] F Aryl fluondes have been prepared from p YC6H4N" (CH3)3CF3S03- (Y = COCqHs, CN, CHO, NO2, COCH3, CO2C2H5) by this alternative substrate Fluorodequaternization can also be applied to the preparation of fluonnated heterocyclics such as 4 fluoro 6 phenyl 1,3 pyrimidine [76] (equation 15) and fluoropunnes [77]... 

Quinazolines substituted in the pyrimidine ring with fluoro, bromo, or iodo atoms are not known. 

Acylation of mesoionic pyrido[l,2-u]pyrimidin-4-ones 150 with aroyl chlorides in the presence of NEts yielded 2-aroyloxy-4//-pyrido[l,2-u]pyrimidin-4-ones 178 (96JHC663). None of the esters 178 could be rearranged to the 2-hydroxy-3-aroyl derivatives 179. The hydroxy group of 9-hydroxy-2-methyl-3- 2-[4-(6-fluoro-l,2-benzisoxazol-3-yl)-l-piperidinyl] ethyl -6,7,8,9-tetrahydro-4//-pyrido[l, 2-u]pyrimidin-4-one was acylated with hexadecanoic acid in CH2CI2 in the presence of dicyclohexylcarbodi-imide and 4-pyrrolidinopyridine at room temperature for 3 days in 80% yield (97MIP7). 

Treatment of 9-(ethoxymethoxy)-3- 2-[4-(6-fluoro-l,2-benzisoxazol-3-yl)-1,2,5,6-tetrahydro-1 -pyridyl] and -1 -piperidyl]ethyl -2-methyl-4/f-pyrido-[1,2-rz]pyrimidin-4-ones with cone. HCl afforded 9-hydroxy derivatives (95MIP4, OOMIPIO). 

Fluorophenyl)-3-fluoro-2-hydroxy-6-oxo-6/7-pyrido[],2-n]pyrimidine-7-carboxylic acid (197, R = 4-FPh, R = H) was obtained from the 2-(4-methyl-]-piperazinyl)-7-ester derivative by the treatment with 1 N NaOH in an 1 1 mixture of H2O and THF at room temperature for 6h (95MIP1, 96JMC3070, 96MIP4, 96USP5580872). 

Heating 6-bromo- and 6-chloro-2-halomethyl- (99JHC1065) and 6-bromo-, 6-chloro- and 6-fluoro-2-phenyl-4/f-pyrido[l, 2-u]pyrimidin-4-ones (00JMC2814) in phenyl ether at 220 °C for 10 min yielded the appropriate 7-halo-1,8-naphthyridin-4-ols. 6-Amino-2-trifluoromethyl-4//-pyrido[l, 2-a]-pyrimidin-4-one was transformed into 7-amino-2-trifluoromethyl-l,4-dihy-dro-l,8-naphthyridin-4-one in 90% yield (98EJM383). 

It was elaimed that eyelization of ethyl 2-ehloro-5-eyelopropyl-6- [(A-(4,5-dimethoxy-2-nitrophenyl)methoxy)earbonyl]-A-(2-fluoro-3-hydroxy-l-oxo-2-propen-l-yl)amino nieotinate (321) in boiling aqueous dioxane in the presenee of K2CO3 overnight yielded l- [(4,5-dimethoxy-2-nitrophe-nyl)methoxy]earbonyl -9-eyelopropyl-3-fluoro-2-oxo-2,6-dihydropyrido[l, 2-n]pyrimidine-7-earboxylate (160) (95MIP1, 96MIP4, 96USP5580872). 

Cyclopropyl-3-fluoro-2-hydroxy-6-oxo-6//-pyrido[l,2-n]pyrimidine-7-carboxylates 340 were obtained in the reaction of 2-cyclopropyl-2-(5-fluoro-4-hydroxy-2-pyrimidinyl)acetaldehyde (339) and ethyl, rerr-butyl and dibenzyl malonates in the presence of piperidine and AcOH (95MIP1, 96JMC3070, 96MIP4, 96USP5580872). 

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