Synthetic Route of 1780-26-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1780-26-3, name is 2-Methyl-4,6-dichloropyrimidine. A new synthetic method of this compound is introduced below.
To the stirred solution of 2-amino-N-(2-chloro-6-methylphenyl)thiazole-5- carboxamide 9 (15.0 g, 0.06 mol) and 4,6-dichloro-2-methylpyrimidine (10.9 g, 0.07 mol) in tetrahydrofuran (THF) (150.0 mL) was added a 29% wt.solution of NaOtBu in THF (64.9 g, 0.2 mol) at 10-20C, over 15-20 minutes. The mixture was stirred at room temperature for 1h and cooled to 0-5C. 1N Hydrochloric acid (~90.0 mL) was added slowly to pH 2-3 followedby the added water 90.0 mL) and stirred for 2h at 0-5C, product was filtered and washed the wet cake with water (60.0 mL) followed by acetone (30.0 mL) gave 5 (20.7 g, 94%).UV (Methanol): max, 319.6 & 203.2 nm; IR (KBr, cm-1): 3420.3 (N-H), 3016.6 (Ar C-H), 1638.6 (C=O); 1H NMR spectrum (400 MHz, DMSO-d6), delta, ppm (J, Hz): 12.23 (s, 1H, thiazole-NH), 10.02 (s, 1H, amide-NH), 8.32 (s,1H, thiazole-H), 7.42-7.40 (m, 1H, Ar-H), 7.31-7.25 (m, 2H, J =7.5, Ar-H), 6.95 (s, 1H, pyrimidine-H), 2.59 (s,3H, Ar-CH3), 2.25 (s, 3H, pyrimidine-CH3); 13C NMR spectrum (100 MHz, DMSO-d6), delta, ppm: 167.4(pyrimidine-C), 161.2 (pyrimidine-C), 159.5 (pyrimidine-C), 158.5 (amide-C), 157.6 (thiazole-C), 140.8 (Ar-C),138.8 (thiazole-C), 133.3 (Ar-C), 132.4 (Ar-C), 129.0 (Ar-C), 128.3 (Ar-C), 127.2 (thiazole-C), 103.4 (pyrimidine-C), 67.0 (pyrimidine-C), 25.2 (Ar-CH3), 18.3 (pyrimidine-CH3); MS (ESI) m/z 391.9 [M – H] – [5].
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1780-26-3, 2-Methyl-4,6-dichloropyrimidine, and friends who are interested can also refer to it.
Reference:
Article; Suresh, Garbapu; Nadh, Ratnakaram Venkata; Srinivasu, Navuluri; Yennity, Durgaprasad; Synthetic Communications; vol. 47; 17; (2017); p. 1610 – 1621;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia