2,6-dimethyl amidinate

Other ways to prepare this drug and similar compounds are summarized in Scheme 5.96 [553]. Arylalkyl nitriles (409) reacted with trimethyloxonium tetrafluoroborate in nitromethane to form the methylnitrilium salts (410). Treatment with methylamine then gave the dimethyl amidines (411) (R ,... 

Amidines react with P-keto esters to provide hydroxypyrimidines. The synthesis of the 2,6-dimethyl-4-hydroxylpyrimidine (9) has been improved dramatically by combining Pinner s procedure with that of Donleavy et al. for the synthesis of 6-methyluracil. 

The amidines 10, prepared by condensation of the corresponding imidates with aminoacetal-dehyde dimethyl acetal, undergo cyclization with a variety of acids to l//-3-benzazcpin-2-amines 11 45 Method A has proved to be successful on an industrial scale. 

Using the preorganized bis(amidinate) ligands featuring 9,9-dimethyl-xanthene backbones, several new dizirconium complexes have been prepared. For example, hexa(amido) complexes were obtained by reaction of the ligands with 2 equivalents of Zr(NMe2)4 (Scheme 212). ... 

Substituted pyrimidine N-oxides such as 891 are converted analogously into their corresponding 4-substituted 2-cyano pyrimidines 892 and 4-substituted 6-cya-no pyrimidines 893 [18]. Likewise 2,4-substituted pyrimidine N-oxides 894 afford the 2,4-substituted 6-cyano pyrimidines 895 whereas the 2,6-dimethylpyrimidine-N-oxide 896 gives the 2,6-dimethyl-4-cyanopyrimidine 897 [18, 19] (Scheme 7.6). The 4,5-disubstituted pyridine N-oxides 898 are converted into 2-cyano-4,5-disubsti-tuted pyrimidines 899 and 4,5-disubstituted-6-cyano pyrimidines 900 [19] (Scheme 7.6). Whereas with most of the 4,5-substituents in 898 the 6-cyano pyrimidines 900 are formed nearly exclusively, combination of a 4-methoxy substituent with a 5-methoxy, 5-phenyl, 5-methyl, or 5-halo substituent gives rise to the exclusive formation of the 2-cyanopyrimidines 899 [19] (Scheme 7.6). The chemistry of pyrimidine N-oxides has been reviewed [20]. In the pyrazine series, 3-aminopyrazine N-ox-ide 901 affords, with TCS 14, NaCN, and triethylamine in DMF, 3-amino-2-cyano-pyrazine 902 in 80% yield and 5% amidine 903 [21, 22] which is apparently formed by reaction of the amino group in 902 with DMF in the presence of TCS 14 [23] (Scheme 7.7) (cf. also Section 4.2.2). Other 3-substituted pyrazine N-oxides react with 18 under a variety of conditions, e.g. in the presence of ZnBr2 [22]. 

The zinc complex formed with V,V -diphenylformamidinate is structurally analogous to the basic zinc acetate structure, as [Zn4(/i4-0)L6], and the basic beryllium acetate structure. It is prepared by hydrolysis of zinc bis(diphenylformamidinate).184 Mixed metal zinc lithium species were assembled from dimethyl zinc, t-butyl lithium, V.iV -diphenylbenzamidine and molecular oxygen. The amidinate compounds formed are dependent on the solvent and conditions. Zn2Li2 and... 

Bromonitromethane is used for the preparation of nitrocyclopropane. The reaction of /V-be 11 zylmaleimide and bromonitromethane in the presence of base gives the azabicyclo[3.1.0] hexane ring system. Many bases have been tried to improve the yield however, amidine base, particularly 1,2-dimethyl-l, 4, 5, 6-tetrahydropyrimidine (DMTHP), gives the best yield... 

Dimethyl pimelimidate (DMP) is a homobifunctional crosslinking agent that has imidoester groups on either end (Thermo Fisher). The imidoesters are amine reactive to give stable amidine linkages with target molecules. The 7-atom bridge created by DMP crosslinks is non-cleavable and... 

When the side chain involves an unsymmetrical urea moiety, muscle relaxant activity is often seen. One such agent, 1id-amidine (2) exerts its activity as an antiperistaltic agent. Its synthesis involves the straightforward reaction of 2,6-dimethyl phenyl isocyanate and ji-methylguanidine. ... 

The syntheses of 9-deazahypoxanthines 225 from pyrroles 224 have been carried out by allowing the amino group of 224 to react with DMF dimethyl acetal (Equation 80). The intermediate amidine readily undergoes cyclization to give 225 <1994JME2477>. Other examples following this type of reaction are known <2000CHE1409>. 

Amidines formed by condensation of 4-aminouracils with dimethylformamide dimethyl acetal are effective dienophiles, and form pyrimido[4,5-rflpyrimidines by [4-I-2] cycloaddition with isocyanates, isothiocyanates (Equation 83) <2005TL1433> and imines (Equation 84), A similar process has also been reported, using a nitrone as the dienophile (Equation 85) <2006BMCL3537>. 

Dimethyl ami no)-2-azaprop-2-en-l-yl ideneldimethylammonium chloride ("Gold s reagent"),4 the preparation of which Is described in part A of the procedure, is a general B-dimethylaminomethylenating agent which reacts successfully with amines (eq. 1) to produce amidines, with ketones (eq. 2) to produce enaminones,6 and with amides (eq. 3) to product acyl ami dines. ... 

Further extension of this synthesis to guanidines leads to 3,5-diamino-l,2,4-thiadiazoles. Examples are so far confined to the conversion, by the usual procedure, of 2V,2V-disubstituted guanidines into 5-amino-3-dialkyl(or diphenyl)amino-l,2,4-thiadiazoles (66).84,87 In general, this variant of the reaction proceeds less uniformly than with amidines or iso(thio)ureas, and is performed without isolation of the intermediate AT-halogenoguanidines. In some cases (e.g. dimethyl and cyclopentamethylene homologs) the yields are low, and guanidine is formed as a by-product. The 3-dimethylamino homolog (66 R = R ... 

Condensation of amine 277 with dimethylformamide dimethylacetal (DMF/DMA) gave A, A-dimethyl-./V -(5-methyl-l, 2,4-triazolo[l, 5-a]pyrim-idin-7-yl)formamidine (278), whose reaction with hydroxylamine gave the formamidoxime 279 (89EGP264438 90ZC320).The amine 280 and the hydrazine 282 can be transformed into the amidine 281 and amidrazone 283, respectively (90ZC320) (Scheme 54). 

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