Reference of 49845-33-2 ,Some common heterocyclic compound, 49845-33-2, molecular formula is C4HCl2N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a mixture of 2,4-dichloro-5-nitropyrimidine (4) (50.0 g, 258 mmol) and 3*HCl (55.5 g, 284 mmol) in toluene (500 mL) was added NaHCO3 (54.1 g, 644 mmol), and the mixture was stirred at 85-95 C for 3 h under N2 atmosphere. After cooling to room temperature, the mixture was filtered and insoluble matter was washed with toluene (50 mL). To the combined filtrate was added H2O (250 mL), and the layers were separated. To the organic layer were added EtOAc (250 mL) and 1 M HCl (250 mL), and the layers were separated. The organic layer was concentrated in vacuo until the weight of the mixture became approximately 100 g. To this mixture was added 2-propanol (250 mL), and the mixture was concentrated in vacuo again until the weight of the mixture became approximately 100 g. To the resulting mixture were added 2-propanol (200 mL) and seed crystals of 5 (50.0 mg), and the mixture was stirred at 20-30 C for 1 h. The mixture was cooled to 0-10 C and stirred for 1 h, and then filtrated. Wet solids were washed with 2-propanol/H2O (1:1, 100 mL) and dried in vacuo at 50 C to give 5 (59.7 g, 73%) as a yellow solid. Mp 89-91 C; 1H NMR (600 MHz, CDCl3) delta 1.07 (t, J = 7.6 Hz, 3H), 1.31 (d, J = 6.4 Hz, 3H), 1.36 (d, J = 6.4 Hz, 3H), 1.86-2.04 (m, 1H), 2.37-2.56 (m, 1H), 3.55 (dt, J = 13.1, 6.5 Hz, 1H), 3.75 (s, 3H), 3.78 (t, J = 6.8 Hz, 1H), 8.63 (s, 1H); 13C NMR (151 MHz, CDCl3) delta 12.0, 19.5, 21.6, 23.2, 52.5, 53.7, 58.8, 131.0, 153.5, 156.5, 159.4, 170.8; IR (ATR) 1739, 1572, 1543, 1513, 1466, 1439, 1374, 1345, 1311, 1215, 1197, 1180, 1165, 1084, 993, 912, 866, 767, 559, 445 cm-1; HRMS (ESI): [M+H]+ calcd for C12H18ClN4O4, 317.1011; found, 317.1008. Optical purity: 99.9% ee (chiral HPLC condition A).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 49845-33-2, 2,4-Dichloro-5-nitropyrimidine, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Ishimoto, Kazuhisa; Nakaoka, Keiichiro; Yabe, Osamu; Nishiguchi, Atsuko; Ikemoto, Tomomi; Tetrahedron; vol. 74; 39; (2018); p. 5779 – 5790;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia