Ovcharova, I. M.; Nikolaeva, L. A.; Chaman, E. S.; Golovchinskaya, E. S. published the artcile< Syntheses in the series of purine derivatives. I. Preparation to 2,6-dichloro-9-methylpurine and synthesis of some derivatives of 1,9-dimethylhypoxanthine>, Application In Synthesis of 2382-10-7, the main research area is .
Heating 15 g. 1.9-dimethylisoxanthine (I) 3.5 hrs. with 180 ml. POCl3 at 135° (bath temperature) gave 54.3% 2-chloro-1,9-dimethylhypoxanthine (II, R = Cl). The filtrate from the above product, after distillation of POCl3 in vacuo, treatment with ice, and neutralization gave some 2,6-dichloro-9-methylpurine (IIa), m. 151-2.5°, which was prepared in 62% yield by heating 50 g. I 5 hrs. with 1 l. POCl3 at 140-50°, treating with 57.5 g. PCl5, and heating 9-10 hrs. longer (the sep. addition of POCl3 and PCl5 was essential for good yield). When I was heated with POCl3 in a sealed tube 3 hrs. at 160°, the product after aqueous treatment was 50.85% IIa, also obtained in 65% yield from II (R = Cl) with POCl3-PCl5 as above while heating in sealed tube with POCl3 gave a somewhat lower yield; and in 60% yield from 9-methylisoxanthine (III) with POCl3 in sealed tube. IIa refluxed 6 hrs. with 15% H2SO4 gave 58.3% III, decomposed above 350°, which with CH2N2 gave in 3 days in Et2O an unstated yield of isocaffeine, m. 273-9°. II (R = Cl) refluxed 2 hrs. with EtONa-EtOH gave 81.2% II (R = OEt) m. 192-40. III and SC(NH2)2 in EtOH 10 hrs. gave II (R = SH), m. 289-90°; Na salt dihydrate decomposed above 330°. The mercapto derivative with MeI in 1.5% NaOH 2 hrs. gave II (R = SEt) m. 223-5°. III and 28% NH4OH 5 hrs. at 40-80° gave II (R = NH2) m. 272-7° (HCl salt decomposed 299-302°). Similarly was prepared II (R, m.p., and m.p. HCl salt given): PhCH2NH, 206-8°, 246-50° (decomposition) EtNH, 199-201°, 285-7° (decomposition); Me2N, 149-51°, 224-50°; Et2N, 105-7°, 179-81° (decomposition). This reactivity of Cl in 2-position is explained by the electron donor groups in the 6-position of the ring.
Zhurnal Obshchei Khimii published new progress about 2382-10-7. 2382-10-7 belongs to class chlorides-buliding-blocks, and the molecular formula is C6H4Cl2N4, Application In Synthesis of 2382-10-7.
Referemce:
Chloride – Wikipedia,
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