Synthesis of 2-(p-aminophenylsulfonamido)4,5-dimethyl-pyrimidine was written by Sugasawa, Shigehiko;Yamada, Shun-ichi;Narahashi, Masuko. And the article was included in Yakugaku Zasshi in 1951.SDS of cas: 1193-74-4 This article mentions the following:
A suspension of 23 g. Na powder in 400 ml. C6H6 treated with 60 g. HCO2Me and 72 g. MeCOEt dropwise at 5-10°, stirred 3 hrs., 150 ml. C6H6 added, the mixture poured slowly into 118 g. concentrated H2SO4 and 128 g. dry MeOH at 10°, stirred 4 hrs., neutralized with Na2CO3, filtered, and the filtrate distilled give 42.4 g. AcCHMeCH(OR)2 (I) (R = Me), b8 68-73°; 30 ml. absolute alc., 6 g. CaCl2, and 3 g. AcCHMeCHO in 2 ml. EtOH at 0-2°, let stand in a refrigerator 2 days, the alc. removed, and the residue taken up with ether and distilled give 2.5 g. I (R = Et), b8 81-4°. AcC(:CHONa)Me (II) (58 g.) in 120 ml. water treated with 42 g. Me2SO4 dropwise, kept 2 hrs. at 60-5°, extracted with C6H6, and the extract distilled give 22.3 g. AcCMe:CHOR (III) (R = Me), b4 62-4°; II with EtBr and p-MeC6H4SO2Et in EtOH give III (R = Et), b5 71-5°. (CH2OH)2, (7.4 g.), 20.2 g. concentrated H2SO4, and 60 ml. C6H6 at 4-5° treated dropwise with 24.4 g. II, the mixture stirred 4 hrs., poured into water containing NaHCO3, extracted with CHCl3, and the extract distilled give 2.5 g. AcCHMeCH.O.CH2.CH2.O, b4 74-7°. Guanidine HNO3 (0.56 g.) added to 0.12 g. Na in 6 ml. EtOH, the mixture filtered, the filtrate refluxed 2 hrs. with 0.6 g. I (R = Me), 0.12 g. Na, and 3 ml. EtOH, water added, the solution extracted with CHCl3, and the product recrystallized from water give 0.2 g. 2-amino-4,5-dimethylpyrimidine (IV), m. 215-16°. p-AcHNC6H4SO2NHC(:NH)NH2 (V) (7 g.) in 70 ml. glacial AcOH refluxed 5 hrs. with 4 g. I (R = Me) in 10 ml. AcOH, the AcOH removed, water added, the mixture filtered, 5% NaOH added, the precipitated V filtered, and the filtrate acidified with AcOH give 6.1 g. 2-(p-AcHNC6H4SO2NH) analog (VI) of IV, m. 270. Refluxing 1 g. VI 1 hr. in 10 ml. 10% NaOH, filtering with C, and acidifying the filtrate with AcOH give 0.7 g. 2-(p-H2NC6H4SO2NH) analog (VII) of VI, m. 220°. p-Me2NC6H4SO2NH2 (2 g.) and 1.17 g. guanidine carbonate heated 1.5 hrs. at 210°, 5% NaOH added, and the mixture filtered give 1.9 g. p-Me2NC6H4SO2NHC(:NH)NH2 (VIII), m. 248°. VIII (0.9 g.), 0.37 g. AcCHMeCHO, and 70 g. BuOH heated in a sealed tube 7 hrs. at 120°, the mixt filtered, the solid taken up in 10% NaOH, filtered, and the filtrate acidified with AcOH give 0.51 g. 2-(p-Me2NC6H4SO2NH) analog (IX) of IV, m. 235°. Letting 1.3 g. urea in 50 ml. EtOH, 3.6 g. I (R = Et), and 7 ml. concentrated HCl stand on ice several days gives 1.3 g. 2-HO analog (X) of IV; HCl salt, decompose 250°. X (4 g.) in 10% KOH evaporated to dryness, the residue added to 20 ml. POCl3 with ice cooling, the mixture heated on an oil bath 3 hrs., the POCl3 removed in vacuo, and the residue poured in ice water, neutralized with NaOH, and with C6H6 gives 1.3 g. 2-Cl analog (XI) of IV, m. 22.5-6°. In the experiment, the researchers used many compounds, for example, 4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4SDS of cas: 1193-74-4).
4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.SDS of cas: 1193-74-4
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia