Reference of 514854-13-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.514854-13-8, name is 6-Ethyl-5-iodopyrimidine-2,4-diamine, molecular formula is C6H9IN4, molecular weight is 264.07, as common compound, the synthetic route is as follows.
According to a general Sonogahisra coupling procedure, ethyl-iodopyrimidine (0.105 g, 0.4 mmol), CuI (0.028 g, 0.08 mmol, 21 mol %), Pd(PPh3)2Cl2 (0.028 g, 0.04 mmol, 10 mol %) and alkyne 45 (0.123 g, 0.6 mmol) were reacted in DMF/Et3N (1.3 mL each) at 60 C. for 12 h. After the mixture was cooled, dark reddish brown solution was concentrated and the product was purified by flash chromatography (SiO2, 5 g, 2% MeOH/CHCl3) to afford coupled pyrimidine 48 as a pale white powder (0.099 g, 71%) followed by reverse phase flash chromatography (NH2 capped SiO2, 3 g, 100% CH2Cl2, 1% MeOH/CH2Cl2) for biological evaluation: TLC Rf=0.1 (5% MeOH/CH2Cl2); mp 161.3-162.8 C.; 1H NMR (500 MHz, CDCl3) delta 8.84 (s, 2H), 8.62-8.02 (m, 2H), 7.88-7.37 (m, 3H), 5.16 (s, 2H), 4.98 (s, 2H), 4.10 (q, J=7.1 Hz, 1H), 2.67 (q, J=7.6 Hz, 2H), 1.65 (d, J=7.2 Hz, 3H), 1.22 (t, J=7.6 Hz, 3H); 13C NMR (12 MHz, CDCl3) delta 174.1, 164.4, 163.8, 161.1, 156.1, 137.5, 133.9, 130.9, 128.8, 128.3, 99.2, 89.9, 29.9, 28.7, 24.3, 12.7; IR (neat cm-1) 3401, 3312, 3159, 2970, 2933, 2871, 2222, 1623, 1563, 1427, 802, 740, 687; HRMS (ESI, M++H) m/z 345.1817 (calculated for C20H21N6, 345.1822); HPLC (a) tR=6.7 mins, 99.6%, (b) tR=7.6 mins, 99.6%
The chemical industry reduces the impact on the environment during synthesis 514854-13-8, I believe this compound will play a more active role in future production and life.
Reference:
Patent; Wright, Dennis L.; Anderson, Amy C.; Sormunen, Grant; US2015/225353; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia