Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Zb. Prikl. Khim. called Synthesis of 2,4-dimethyl-3-hydroxy-5-hydroxymethylpyridine, Author is Balyakina, M. V.; Rubtsov, I. A.; Zhdanovich, E. S.; Preobrazhenskii, N. A., which mentions a compound: 148-51-6, SMILESS is OC1=C(C)C(CO)=CN=C1C.[H]Cl, Molecular C8H12ClNO2, Application of 148-51-6.
2,4-Dimethyl- 3 – hydroxy-5- hydroxymethylpyridine (4- deoxypyridoxine) (I) was synthesized via the following intermediates: 2,4-dimethyl-5-cyano-6-pyridone (II), 2,4-dimethyl-3-nitro-5-cyano-6-pyridone (III), and 2,4-dimethyl-3-nitro-5-cyano-6-chloropyridine (IV). Reduction of IV was carried out in 1 step in dilute HCl over Pd-C. 2,4-Dimethyl-3-amino-5-aminomethylpyridine was converted without isolation to I by treatment with NaNO2. Thus, 33 ml. NH4OH (d20 0.9) was added with stirring to 40 g. EtO2CCH2CN, the mixture cooled with ice to 0-2° and the precipitate filtered off, washed at 0° with 20 ml. cold EtOH, and dried to yield 23.8 g. cyanoacetamide (V), m. 120-2°. The filtrate was evaporated to dryness to yield an addnl. 3.95 g. Acetylacetone (10.0 g.) was added at 70° to 8.4 g. V in 50 ml. MeOH and 1.12 ml. Me2NH to precipitate 88.1% II, m. 293.1-4.2°. A suspension of 4.44 g. II in 15 ml. Ac2O is treated with stirring with 2.3 ml. HNO3 (d20 1.4) and 2.3 ml. Ac2O at 35-40°, and the mixture stirred 2 hrs. at 18-20° and poured upon 23 g. crushed ice, to precipitate 56.4% yellow III, m. 272.0-2.6° (alc.). P2O5 (5.3 g.) is added to a suspension of 3.6 g. III in 36 ml. PhCl, the mixture heated with stirring 3 hrs. at 118-120° the solvent removed at 45-50°/10 mm., the residue treated with 3.6 ml. absolute alc., stirred, and left 8 hrs. at 0-4°, the precipitate filtered off, washed at 0° with 2 ml. alc., and dried, and the residue extracted with petr. ether (b. 60-70°) to give 62.2% yellow IV, m. 114-15°. IV (2.4 g.) in 25 ml. ice water was added to a pre-hydrogenated mixture of 0.10 g. PdCl2 with H2O, HCl, and C, the hydrogenation continued until the theoretical H absorption, the catalyst separated and washed with 2 ml. H2O, 2.4 ml. HCl (d20 1.18) added to the solution and washings, and the solution heated 1.5 hrs. at 80-5° during which 1.6 g. NaNO2 in 5 ml. H2O was added, the heating continued 30 more min. (neg. starch-iodide test), the solution evaporated in vacuo, the residue extracted with absolute alc., the extracts treated with activated C and concentrated until the appearance of crystals, the mixture kept 8 hrs. at 0-4°, and the precipitate filtered off, washed at 0° with 1 ml. alc., and dried to give 42.2% I, m. 256.1-7.2°.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia