Pyrimidines, nitro-, synthesis

Pyrimidine, 5-benzyl-4,6-dimethyl-2-phenyl-synthesis, 3, 118 Pyrimidine, 2-benzyl-5-nitro-synthesis, 3, 130 Pyrimidine, benzyloxy-pyrimidinone synthesis from, 3, 133 Pyrimidine, 4,5-bis(alkylamino)-synthesis, 3, 121 Pyrimidine, 2-bromo-aminolysis, 3, 100 H NMR, 3, 62 reactions... 

Pyrimidine, 2-methylthio-5-nitro-aminolysis, 3, 96 Pyrimidine, nitro-reactivity, 3, 84-88 synthesis, 3, 130 Pyrimidine, 3-nitro-synthesis, 2, 504 Pyrimidine, 5-nitro-cation... 

Pyrimidin-2-amine, 4-ethyI-5-(2 -hydroxy-4 -nitrophenyI)-6-methyl-synthesis, 3, 121 Pyrimidin-2-amine, 4-methyl-basic pXj, 3, 61 Pyrimidin-2-amine, N-methyl-hydrolysis, 3, 84 synthesis, 3, 135 Pyrimidin-2-amine, 5-nitro-basic pXj, 3, 61 hydrolysis, 3, 84 Pyrimidin-2-amine, 4-phenyl-synthesis, 3, 109 Pyrimidin-2-amine, 5-phenyl-nitration, 3, 78... 

Pyrimidin-4-amine, 5-nitro-2-styryI-reduction, 3, 88 Pyrimidin-4-amine, 2-phenyl-hydrolysis, 3, 84 Pyrimidin-4-amine, 5-phenyI-synthesis, 3, 116 Pyrimidin-4-amine, triphenyl-synthesis, 3, 119... 

Pyrimidine-4(3H)-thione, 6-methoxy-5-nitro-reduction, 3, 88 Pyrimidinethiones acidic pK, 3, 60 S-acylation, 3, 95 N-alkylated synthesis, 3, 139 aminolysis, 3, 94 desulfurization, 3, 93 electrophilic reactions, 3, 69 hydrolysis, 3, 94 oxidation, 3, 94, 138 pyrimidinone synthesis from, 3, 133 reactions... 

Of greater versatility is an extension of Albert and Royer s acridine synthesis. The first successful use of this in the quinazoline series was for the removal of the chlorine atom in 2-chloro-4-phenylquin-azoline, although it had been used previously to prepare 8-nitro-6-methoxyquinazoline in very poor yield. The 4-chloroquinazoline is converted to its 4-(A -toluene-p-sulfonylhydrazino) quinazoline hydrochloride derivative which is decomposed with alkali in aqueous ethylene glycol at lOO C (Scheme 13). The yields are high (60-70%) when R is Me, Cl, OMe but low when R is NO2, and in the latter case it is preferable to use dilute sodium carbonate as the base. This reaction is unsatisfactory if the unsubstituted pyrimidine ring is unstable towards alkali, as in 1,3,8-triazanaphthalene where the pyrimi-... 

Reduction is used for carbonyl functionalities [71, 230] such as thioesters [231], amides [232], and carbamates [233], as well as for sulfur [234] and selenium [122] compounds. Recently, the synthesis of a potential carbohydrate vaccine is described via an reduction-oxidation sequence [235]. An efficient solid-phase synthesis of pyrimidine derivatives that involved reduction of the corresponding nitro derivatives was developed by Makara et al. in 2001 (Scheme 3.9) [236]. 

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