5- Cyano-6-methylpyrimidine

Cyclization of 5-cyano-6-methylpyrimidine-2,4(l//,3H)-diones 136 with elemental sulfur generated the corresponding 5-aminothieno[3,4-d]-pyrimidine-2,4(l//,3//)-diones 137 (90MI1 91MI2). Similarly, cyclization of 5-cyanopyrimidine-4(3H)-thiones 138 with sulfur afforded the 5-amino-4-thioxo derivative 139 (90LA1215). 

The creation of a thiophene ring from 0/7/w-cyano-methylpyrimidines has provided access to thieno[3,4-c/]pyrimidines. Mono- or di-iV-(substituted)uracils (278) undergo reaction with elemental... 

Cyclocondenzation of 2-pyridylacetonitrile and ethoxycarbonyl isothiocyanate in MeCN gave 4-cyano-l-oxo-2,3-dihydro-lH-pyrido[l,2-c]pyrimi-dine-3-thione in 18% yield (08MI2). 6-Endo-trig cyclization of anion, formed from 4-methylpyrimidine by LDA in THF at —78 °C, with methyl 3-propynoate provided 8-methyl-6H-pyrido[2,l-c]pyrimidin-6-one in 47% yield (06TL5063). 

To diethoxymethoxy-ethane malononitrile was added and ethoxymethylen-malononitrile was obtained. The ethoxymethylen-malononitrile reacted with acetamidine as a result 4-amino-5-cyano-2-methylpyrimidine was produced, which was reduced by H2/Raney-Ni to 4-amino-5-aminomethyl-2-methylpyrimidine. 

Figure 2. Formulas of selected D-A compounds which contain 4-dialkylamino group as an electron donor and reveal dual fluorescence behaviour. Top /)-cyano-A,A-dimethylaniline (I, CDMA) and its model derivatives p-cyano-2,A,A-trimethylaniline (II), p-cyano-2,6,A.A-tetramethylaniline (III, CTMA)./)-aminobenzonitrile (IV, ABN) and l-ethyl-2,3-dihydro-indole-5-carbonitrile (V. BIN). Middle 4-(dimethylamino)pyrimidine (VI), 4-(diethylamino)pyrimidine (VTI), 4-(dimethylamino)-5-methylpyrimidine (VIII), 4-(diethylamino)-5-methylpyrimidine (IX) and 4-(dimethylamino)-pyridine (X). Bottom methyl 4-(dimethylamino)benzoate (XI, DMAMB), ethyl 4-(dimethylamino)benzoate (XII, DMAEB), p-(dimethylamino)-benzaldehyde (XIll) and />-(dimethylamino)acetophenone (XIV).

As for medicinal applications, some pyrimidines were prepared as potential antiviral agents. Among them were 2,4-diamino-5-cyano-6-[2-(phosphonomethoxy)ethoxy]pyrimidines 83a,b <04BMC3197>, imidazo[l,2-c]pyrimidine base-modified nucleoside mimetics 84a-c and 85a-c <04BMC4245>, (Z)- and ( )-[2-fluoro-2-(hydroxymethyl)cyclopropylidene]methylpyrimidines <04JMC6964>, (Z)- and ( )-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpyrimidines... 

Antonova and coworkers reported the electroreduction of 4-amino-5-cyano-2-methylpyrimidine to the corresponding amine in acidic aqueous medium. A competitive pathway due to hydrolysis of the intermediate aldimine may occur yielding an aldehyde or an alcohol (Scheme 14). A Ni cathode in HCl solution containing PdCh and substrate at 20 °C and current densities of 2A dm" gave the maximum yield (84%) of the expected amine. It is noteworthy that Pd is electrodeposited on the electrode at the beginning of the... 

Amino-5-cyano-2-methylpyrimidine, is an intermediate used in a synthesis (section 21.14.2.3) of thiamin (vitamin Bj). 

Ethyl ethoxymethylenecyanoacetate treated with 3 equivalents of acetamidine in ethanol with cooling, then kept overnight in a refrigerator 5-cyano-4-hydroxy-2-methylpyrimidine acetamidinate. Y 85.5%. F. e. and different reaction course s. S. Nishigaki et al., Tetrah. Let. 1969, 247. 

Amino-5-cyano-2-methylpyrimidine is an intermediate used in a synthesis... 

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