Reference of 1004-38-2 ,Some common heterocyclic compound, 1004-38-2, molecular formula is C4H7N5, 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.
In some exemplary embodiments, 65 mL of concentrated hydrochloric acid was added to a solution of 5.0 g, 0.036 mol ortho-nitroaniline in 75 mL dimethyl formamide dropwise. The solution was stirred for 10 minutes at 3 C. 2.5 g, 0.036 mol of sodium nitrite in 18 mL of water was added dropwise to the solution. The resulting clear yellow solution was stirred for 30 minutes at 3 C. 4.53 g, 0.036 mol of 2,4,6-triaminopyrimidine was added in portions over 5 minutes. Orange/red precipitate forms with each addition of pyrimidine. 100 mL of water was added. The resulting orange/yellow heterogeneous mixture was gradually warmed to room temperature for approximately 20 hours with vigorous stirring. Filtration of the resulting orange slurry gave an HCl salt of azo, which was washed with ice-chilled water. The resulting pasty material was stirred vigorously with 450 mL of 10% potassium carbonate for 30 minutes at room temperature. The resulting red precipitate was filtered, washed with water, and air dried over several days or dried in a vacuum oven at 70 C. and 25 mmHg to give a yield of 8.86 g (90%) azo. The material was characterized as follows: mp 274 C. (broad dec); 1H NMR (300 MHz, DMSO-d6) delta 9.54 (s, 1H), 8.23 (dd, J=8.4, 0.9 Hz, 1H), 7.89-7.80 (m, 2H), 7.62 (td, J=8.4, 1.2 Hz, 1H), 7.34 (m, 2H), 7.01 (s, 1H), 6.74 (s, 2H); 13C NMR (75 MHz, DMSO-d6) delta 165.0, 164.5, 155.8, 145.9, 145.5, 133.7, 126.8, 124.7, 118.4, 113.0; IR: 3505, 3392, 3096, 1666, 1619, 1569, 1510, 1435, 1351, 1257, 1215 cm-1; MS-DART ionization-positive (m/z): calculated for C10H11N8O2 [M+H]+, 275.1005; found, 275.0970. Anal. Calcd. for C10H10N8O2: C, 43.80; H, 3.68; N, 40.86; Found: C, 42.68; H, 3.58; N, 39.20.
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. 1004-38-2, 2,4,6-Triaminopyrimidine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; The United States of America as Represented by the Secretary of the Navy; US8273877; (2012); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia