《Pyrimidine synthesis from ethyl ethoxymethylenecyanoacetate and amidines》 was published in Tetrahedron Letters in 1969. These research results belong to Nishigaki, Sadao; Aida, Kyoko; Senga, Keitaro; Yoneda, Fumio. Synthetic Route of C7H10N4O2 The article mentions the following:
Treatment of 1 equivalent EtOH:C(CN)CO2Et(I) with 3 equivalents MeC(:NH)NH2 (II) in cold EtOH and maintaining the mixture at 0° 18 hrs. yielded 85.5% 5-cyano-4-hydroxy-2-methylpyrimidine acetamidinate (III, R = Me) (IV), m. 184-8° (EtOAc). Use of 2 or 1 equivalent II decreased the yields of IV to 69.0 and 20.3%, resp. A small amount of ethyl 4-amino-2-methyl-5-pyrimidinecarboxylate (V) was extracted from the reactions mixtures with Et2O. IV neutralized with AcOH gave 5-cyano-4-hydroxy-2-methylpyrimidine, reconverted to IV by treating with an equimolar amount of II in alc. The mass spectrum of IV revealed the strong parent ions m/e 135, 58 but no mol. ion, m/e 193, corresponding to N-(3-acetamidino-2-cyanoacryloyl)acetamidine, H2NCR:NCH:C(CN)CONHCR:-NH (VI, R = Me) (VII). The reactions of I with 2-ethyl-2-thiopseudourea (VIII) in MeOH readily gave Et 3-[[amino-(ethylthio)methylene]amino]-2-cyanoacrylate (IX); III (R = EtS) (X), m. 175-7°; and traces of V. Increase of the ratio of VIII to I from 1:1 to 4:1 led to decrease of the % yield of IX and increase of X. The reactions of guanidine with I in cold alc. gave predominantly Et 2,4-diamino-5-pyrimidinecarboxylate (XI), m. 215-17° (alc.), along with a trace of III (R = NH2) (XII), m. >300° (MeOH), converted to 2-amino-5-cyano-4-hydroxypyrimidine, m. >300° (AcOH), by treating with AcOH. Use of a large excess of guanidine increased the yield of XI to 95% in the absence of XII. After reading the article, we found that the author used Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1Synthetic Route of C7H10N4O2)
Ethyl 2,4-diaminopyrimidine-5-carboxylate(cas: 15400-54-1) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).Synthetic Route of C7H10N4O2
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia