Categories: Synthesis of N-Heterocycles >
Synthesis of pyrimidines
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Recent Literature
A ZnCl2-catalyzed three-component coupling reaction allows the
synthesis of various 4,5-disubstituted pyrimidine derivatives in a single step
from functionalized enamines, triethyl orthoformate, and ammonium acetate. The
procedure can be successfully applied to the efficient synthesis of mono- and
disubstituted pyrimidine derivatives, using methyl ketone derivatives instead of
enamines.
T. Sasada, F. Kobayashi, N. Sakai, T. Konakahara, Org. Lett., 2009,
11, 2161-2164.
A method for the synthesis of 2-substituted pyrimidine-5-carboxylic esters
is described. The sodium salt of 3,3-dimethoxy-2-methoxycarbonylpropen-1-ol
has been found to react with a variety of amidinium salts to afford the
corresponding 2-substituted pyrimidine-5-carboxylic esters.
P. Zhichkin, D. J. Fairfax, S. A. Eisenbein, Synthesis, 2002, 720-722.
The direct condensation of cyanic acid derivatives with N-vinyl/aryl
amides affords the corresponding C4-heteroatom substituted pyrimidines. The use
of cyanic bromide and thiocyanatomethane in this chemistry provides versatile
azaheterocycles poised for further derivatization.
O. K. Ahmad, M. D. Hill, M. Movassaghi, J. Org. Chem., 2009,
74, 8460-8463.
A novel and efficient synthesis of pyrimidine from β-formyl enamide involves
samarium chloride catalysed cyclisation of β-formyl enamides using urea as
source of ammonia under microwave irradiation.
M. G. Barthakur, M. Borthakur, P. Devi, C. J. Saikia, A. Saikia, U. Bora, A.
Chetia, R. C. Boruah, Synlett, 2007, 223-226.
The coupling of acid chlorides with terminal alkynes using one equivalent of
triethylamine under Sonogashira conditions followed by subsequent addition
of amines or amidinium salts to the intermediate alkynones allows a
straightforward access to enaminones and pyrimidines under mild conditions
and in excellent yields.
A. S. Karpov, T. J. J. Müller, Synthesis, 2003, 2815-2826.
A single-step conversion of various N-vinyl and N-aryl amides
to the corresponding pyrimidine and quinazoline derivatives involves amide
activation with 2-chloropyridine and trifluoromethanesulfonic anhydride
followed by nitrile addition into the reactive intermediate and
cycloisomerization.
M. Movassaghi, M. D. Hill, J. Am. Chem. Soc., 2006, 128, 14254-14255.
An array of tetrasubstituted saturated fused pyrimidines has been synthesized
through a simple and efficient one-pot operation. The strategic utilization of
the N-PMB group enabled the construction of a broad range of N-vinyl
tertiary enamide starting materials. This stands as a flexible approach to
functionalized pyrimidines with the capability of manipulating either ketone,
acid chloride, or nitrile reaction partners.
A. A. Estrada, J. P. Lyssikatos, F. St-Jean, P. Bergeron, Synlett, 2011,
2387-2391.
