Three-component process for the synthesis of 4-amino-5- pyrimidinecarbonitriles under thermal aqueous conditions or microwave irradiation

Abstract

The three-component reaction of malononitrile, aldehydes and N-unsubstituted amidines, is extended to the formation of 4-amino-5-pyrimidinecarbonitrile derivatives. The reaction occurs in water at reflux or under microwave heating, in the presence of sodium acetate. This method provides a new route to produce pyrimidine derivatives in good to excellent yields.

Effects of different types of nuclear radiations on optically stimulated luminescence

“…50 Furthermore, another 1-pot synthesis of 2,4-diamino-6-arylpyrimidine-5-carbonitriles 79 was reported by Deshmukh 2,6-Diamino-4-arylpyrimidine-5-carbonitriles 79 were also synthesized by 3-component reaction of malononitrile 27, aldehydes 4, and guanidinium chloride 8 in water at reflux or under microwave heating, in the presence of sodium acetate. 52 Sheibani and co-workers reported another method for synthesis of this class of compounds using high-surface-area MgO as a highly effective heterogeneous base catalyst. 53 Moreover, an efficient 1-pot synthesis of 2,6-diamino-4-arylpyrimidine-5-carbonitriles 79 has been achieved in excellent yields by the condensation of malononitrile 27, aldehydes 4, and guanidinium chloride 8 using ionic liquid under controlled microwave irradiation (100 W) at 60 • C. 54 One-pot synthesis of 6-alkylamino-2,4-diaminopyrimidines 82 using ketene dithioacetals 80, 55 There are 2 more methods for synthesis of the above 2-amino-5,6-dihydropyrimidin-4(3H)-ones 61.…”

Three-Component Synthesis of Fluorinated Pyrimidine Carbonitrile Derivatives under Thermal Aqueous Conditions

“…6 The increasing importance of pyrimidines and their derivatives as intermediates for the synthesis of biologically and industrially useful compounds prompted us to synthesise 4-aminopyrimidine-5-carbonitrile derivatives. 7 Peters et al, 8,9 have reported the synthesis of 5-aminomethylpyrimidines with small substituents (Me, Cl, MeO, F and CF 3 ) in different positions at phenyl rings by reducing 5-cyanopyrimidines, which were obtained in a first step by the reaction of benzylamidines and arylidenemalononitriles under basic conditions.…”