Application of 60722-67-0, 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. 60722-67-0, name is 2-(Phenylmethoxy)-4-pyrimidinamine. A new synthetic method of this compound is introduced below.
KHMDS, 0.5M solution in toluene (5.95 mL, 2.98 mmol), was added to a stirred solution of the 2-(benzyloxy)pyrimidin-4-amine (0.50 g, 2.48 mmol) in toluene (15 mL) at 0C under nitrogen atmosphere. The reaction was stirred for 30 mm. In another flask, 4- iodobenzoic acid (1,85 g, 7.44 mmol) was dissolved in CH2CI2 (20 mL) under an N2. The solution was cooled to 0 C, oxalyichloride (0.65 mL, 5.16 mmol) was added dropwise followed by the addition of two drops of DMF. The reaction was allowed to stir for 30 mm, until the solution becomes clear. The mixture was concentrated under reduced pressure; the acid chloride formed was dissolved in dichloromethane (10 mL) added into the deprotonated aminopyrimidine dropwise. The reaction was allowed to warm to rt and was stirred overnight. The reaction was quenched with saturated solution of NH4CI (10 mL), extracted with EtOAc (3 x 10 mL). The combined fractions was washed with brine (10 mL) and dried with anhydrous Na2SO4, filtered and concentrated under reduced presure. Purification on silica gel using flash chromatography (10% EtOAc/hexanes) afforded the desired compound as a white solid. MP. 110 C. 1H NMR (500 MHz, CDCI3); ppm 8.50 (d, IH), 8.48 (br s, 1H), 7.96 (d, 1H), 7.88 (d, 2H), 7.60 (d, 2H), 7.47 (d, 2H), 7.38 (t, 2H), 7.34 (t, IH), 5.43 (s, 2H). ?3C NMR (100 MHz, CDCI3); ppm 165.4, 164.7, 160.9, 159.2, 138.5, 136.4, 132.8,128.9, 128.6, 128.2, 128.0, 104.4, 100.6, 69.3. IR(neat); 3303, 3061, 1695, 1585, 1516, 1402, 1288 cm-?. HRMS (ES) Calculated for C,8H,4N3O2Na1 m/z (M+Na) 454.0028, Obs?d.454.0030.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,60722-67-0, 2-(Phenylmethoxy)-4-pyrimidinamine, and friends who are interested can also refer to it.
Reference:
Patent; CURZA GLOBAL, LLC; THE UNIVERSITY OF UTAH RESEARCH FOUNDATION; REDDY, Hariprasada R. Kanna; SEBAHAR, Paul R.; SERRANO, Catherine M.; LOOPER, Ryan E.; (117 pag.)WO2019/13789; (2019); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia