Brown, D. J. published the artcilePyrimidines. I. Spectroscopic studies, Related Products of pyrimidines, the publication is Journal of the Chemical Society (1953), 331-7, database is CAplus.
Crude 2-chloropyrimidine (I) (2 g.) and NaOMe (from 0.5 g. Na and 25 ml. MeOH) refluxed 0.5 hr., cooled, saturated with CO2, filtered, the filtrate concentrated in vacuo, the residue extracted with 40 ml. Et2O, and the dried extract concentrated and distilled gave 0.83 g. 2-methoxypyrimidine (II), colorless liquid, b15 70-1°, n20D 1.5060. II (2.4 g.) and 20 ml. 15% Me2NH-MeOH heated 1 hr. at 120°, NaOMe (from 0.4 g. Na in 20 ml. MeOH) added, and the mixture worked up as above (but without refluxing) gave 1.2 g. 2-(dimethylamino)pyrimidine (III), colorless hygroscopic liquid, b17 78-81°, n22D 1.5438. II and MeNH2-EtOH similarly gave 2-(methylamino)pyrimidine (IV), b14 91-2°, m. 59-61° (from petr. ether). 4-Hydroxypyrimidine (V) (7 g.) and 25 ml. POCl3 refluxed 25 min., cooled, extracted with six 15-ml. portions of petr. ether to remove the POCl3, and the residue treated with MeOH gave as with II, 4-methoxypyrimidine (VI), colorless liquid, b30 69-70°. 2,4-Dimercaptopyrimidine (VII) (10.2 g.) and 60 ml. 25% aqueous Me2NH heated 3 hrs. at 130°, evaporated, the residue treated with 200 ml. cold 0.5N HCl (VII was insoluble), the mixture filtered, and the filtrate adjusted to pH 3-4 gave 8.25 g. 4-dimethylamino-2-mercaptopyrimidine (VIII), m. 265-78° (decomposition), which, treated in 370 ml. boiling H2O portionwise with 45 g. (wet weight) Raney Ni, refluxed 0.5 hr., filtered hot, the insoluble material washed with 100 ml. hot H2O, the combined filtrates treated with 20 g. Raney Ni as above, filtered, the filtrate saturated with salt, extracted 15 hrs. with Et2O, and the extracts concentrated and distilled gave 3.1 g. 4-(dimethylamino)pyrimidine (IX), b50 131-2°, m. about 40° 2-Mercapto-4-(methylamino)pyrimidine (12 g.) and Raney Ni as above gave 54% 4-(methylamino)pyrimidine (X), b16 142-4°, m, 69-72° (from petr. ether). 2-Aminopyrimidine (XI) (0.48 g.) and 1.5 ml. Ac2O refluxed 1 hr., cooled, and 5 ml. Me2CO added gave 0.45 g. 2-acetamidopyrimidine, colorless laths, m. 145-6.5° [from AcCH2CHMe (XII)]. 4-Amino-5-cyanopyrimidine (XIII), m. 248-51° (decomposition) (7.4 g.), 55 ml. N KOH, and 225 ml. 3% H2O2 kept 1 hr. at 50-5°, the pH adjusted to 7, and the solution cooled gave 5.6 g. 4-amino-5-pyrimidinecarboxamide, colorless laths, m. 254-6° (from H2O). XIII (1.9 g.) and 19 ml. 2.5N NaOH heated 1 hr. on the steam bath, the pH adjusted to 4, and the whole cooled gave 1.75 g. 4-amino-5 pyrimidinecarboxylic acid (XV), m. 278-81° (from H2O); XIV (4.25 g.) and 40 ml. 2.5N NaOH gave as above 3.8 g. XV. XV (0.5 g.) added in portions to 5 g. Ph2CO at 280, kept 5 min. at 280°, cooled to 100°, 25 ml. petr. ether (b. 100-20°) added, and the mixture cooled gave 0.1 g. 4-aminopyrimidine (XVI), m. 150° (from XII); 4-acetamido analog, colorless needles, m. 198-200° (from XII.). The pKa (for 0.01M solution unless otherwise stated) at 20°, pH (as buffered), λmaximum and log εmaximum for the following compounds are reported: V, 1.69 ± 0.04 (or 8.60 ± 0.02), 13 (or 6.2), 227, 263 (or 223, 260), 4.06, 3.56 (or 3.87, 3.57); VI, 2.5 ± 0.2, 6.95 (0), 247-8 (227-8, 238), 3.53 (3.89, 386); XI (0.1M), 3.54, 7.0 (1), 224, 292 (221, 302-3), 4.13, 350 (4.17, 360); IV 3.82, 0.03, 7.0 (1), 234, 306-7 (228, 315), 4.23, 4.33 (4.23, 3.53); III, 3.96 ± 0.01, 7.0 (1), 243, 318 (235, 324-5), 4.26, 3.35 (4.24, 3.47); XVI (0.005M), 5.71, 13 (0), 233, 268-9 (246), 4.26, 3.72 (4.27); X, 6.12 ± 0.04, 9.0 (2.1), 242, 276-7 (254), 4.18, 3.54 (4.20); and IX, 6.35 ± 0.02, 9.3 (3.15), 250, 286 (262), 4.22, 3.56 (4.21). The infrared absorption curves for 2-hydroxypyrimidine, II, V, and VI in CCl4 are shown; XI and XVI show the 2 strong bands characteristic of the H2N group, proving that these 2 compounds exist in that form in this solvent. The various spectra are discussed.
Journal of the Chemical Society published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Related Products of pyrimidines.
Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia