Tanaka, Kuniyoshi; Sugawa, Toshio; Nakamori, Ritsuo; Sanno, Yasushi; Ando, Yasuo; Imai, Kinichi published the artcile< Nucleic acid antagonists. VI. Synthesis of 1,4,6-triazaindenes (5H-pyrrolo[3,2-d]pyrimidines)>, Recommanded Product: (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is ANTIMETABOLITES; CHEMISTRY, PHARMACEUTICAL; EXPERIMENTAL LAB STUDY; HETEROCYCLIC COMPOUNDS; NUCLEIC ACIDS; PYRIMIDINES; PYRROLES.
Derivatives of 1,4,6-triazaindene, an isostere of purine and indole, were prepared by 2 methods. MeC(:NH)NH2.HCl (11.8 g.) treated with 4.2 g. Na in 85 cc. EtOH and the mixture filtered, treated with 23 g. AcCH(NHAc)CO2Et (I), and heated 4 hrs. on the water bath gave 13.5 g. 2,6-dimethyl-4-hydroxy-5-acetamidopyrimidine (II), m. 275-7° (EtOH). H2NC(:NH)NH2.H2CO3 (4.5 g.) and 1.15 g. Na in 20 cc. EtOH heated 0.5 hr., filtered, treated with 9.35 g. I in 20 cc. EtOH, and heated 8 hrs. on the water bath yielded 3.4 g. 2-NH2 analog of II, m. 295-8° (decomposition). H2NCSNH2 (720 mg.) and 0.5 cc. H2O treated with stirring with 700 mg. Me2SO4 and then with 500 mg. NaOH in 1 cc. H2O and 1.87 g. I and the mixture kept overnight and heated 1 hr. on the water bath gave 700 mg. 2-MeS analog of II, m. 248-52° (EtOH and H2O). II (5 g.) added to 1.9 g. Na in 40 cc. EtOH, the EtOH removed under N, and the residue heated 20 min. under N at 320-5° yielded 2.4 g. 5-Me derivative of III, needles, m. 336° (decomposition). 4-Hydroxy-5-acetamido-6-methylpyrimidine (5 g.) and 2.2 g. Na gave similarly 1.5 g. III, m. above 360°. 5-Benzamido-4-hydroxy-2,6-dimethylpyrimidine (IV) (3.4 g.) and 1.1 g. Na gave similarly during 15 min. at 310° 1.8 g. 2-phenyl-5-methyl-7-oxo-6,7-dihydro-1,4,6-triazaindene, crystal powder, m. 325° (decomposition) (EtOH); also obtained in 60% yield when using iso-PrOH instead of EtOH. 2,4-Diethoxy-6-methyl-5-nitropyrimidine (V) (9.1 g.), 6 g. (CO2Et)2, and 1 g. Na in 20 cc. EtOH heated 1 hr. on the water bath yielded 14 g. yellow precipitate, m. 305° (decomposition); a 13-g. portion, 50 cc. Me2CO, 10 cc. HCl, and 20 cc. H2O refluxed 0.5 hr. gave 1 g. 6-EtO2CCO derivative (VI) of V, m. 115° (decomposition). 2,4-Diallyloxy analog (10 g.) of V and 20 cc. (CO2Et)2 added in a small amount of CH2:CHCH2OH with cooling to 3.2 g. Na in 80 cc. CH2:CHCH2OH and kept at room temperature overnight, and the product dissolved in Me2CO and heated with 10% HCl yielded 12 g. 2,4-diallyloxy analog (VII) of VI, yellow, m. 45° (aqueous EtOH). (CO2Et)2 (5 cc.) and 2 g. 4-amino-2-ethoxy-6-methyl-5-nitropyrimidine in 100 cc. EtOH added to 800 mg. Na in 30 cc. EtOH and heated 3 hrs. on the water bath gave 2.5 g. 4-NH2 analog of VI, yellow, m. 220° (EtOH). VI (10 g.) in 100 cc. AcOEt hydrogenated over Pd-C gave 8 g. 2-carbethoxy-5,7-diethoxy-1,4,6-triazaindene (VIII), m. 141° (Me2CO). VII (3.5 g.) in 35 cc. AcOH treated at 70-80° with 7 g. Zn dust in small portions during 2 hrs., and the oily product (3.1 g.) treated with picric acid yielded the picrate of the 5,7-diallyloxy analog of VIII, yellow, m. 144° (aqueous EtOH). VII (4 g.) in 200 cc. EtOH hydrogenated over Pd-C, and the product heated 6 hrs. with HCl gave 5,7-dioxo-4,5,6,7-tetrahydro-1,4,6-triazaindene-2-carboxylic acid, m. above 360° (H2O). 4-NH2 analog (2 g.) of VI in 300 cc. EtOH hydrogenated over Pd-C gave the 7-NH2 analog of VIII, needles, m. 232° (EtOH).
Chemical & Pharmaceutical Bulletin published new progress about Nucleic acids Role: BIOL (Biological Study). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Recommanded Product: (9Z,12Z)-Methyl octadeca-9,12-dienoate.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics