Adding a certain compound to certain chemical reactions, such as: 1250967-81-7, 2-Chloro-4-isopropoxypyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 1250967-81-7, blongs to pyrimidines compound. HPLC of Formula: C7H9ClN2O
To a RT solution of Intermediate 2 (5 mg, 0.01 mmol) in n-BuOH (0.7 mL) were added 2-chloro-4-isopropoxypyrimidine (4 mg, 0.02 mmol) and iPr2NEt (9 pL, 0.05 mmol). The reaction was stirred at 180 C for 80 min, then was cooled to RT. THF (0.8 mL)/MeOH (0.4 mL)/H20 (0.4 mL) were added to the reaction mixture, followed by LiOH.H20 (3 mg, 0.07 mmol) at RT. The reaction was stirred at RT overnight, then was concentrated in vacuo and the residue was diluted with H20 (5 mL). The pH of the mixture was adjusted with aq. IN HC1 to ~5 and it was extracted with EtOAc (3 x 5 mL). The combined organic extracts were washed with brine (2 mL), dried (MgS04) and concentrated in vacuo. The crude product was purified by preparative LC/MS: Column: Waters XBridge C18, 19 x 200 mm, 5-mha particles; Guard Column: Waters XBridge C18, 19 x 10 mm, 5-pm particles; Mobile Phase A: 5:95 MeCN:H20 with 0.1% TFA; Mobile Phase B: 95:5 MeCN:H20 with 0.1% TFA; Gradient: 15-55% B over 20 min, then a 4-min hold at 100% B; Flow rate: 20 mL/min. Fractions containing the desired product were combined and concentrated via centrifugal evaporation to provide the title compound (6.5 mg, 8.7 pmol, 67 % yield). LCMS, [M+H]+ = 482.3. NMR (500 MHz, DMSO-de) d 8.42 (s, 1H), 8.06 (br s, 1H), 7.93 (s, 1H), 6.23 (br d, J=6.l Hz, 1H), 5.26 – 5.16 (m, 1H), 5.06 (br s, 2H), 4.84 – 4.77 (m, 1H), 3.92 (s, 3H), 2.68 – 2.60 (m, 1H), 2.42 (s, 3H), 2.06 – 1.44 (m, 8H), 1.22 (d, J=6.l Hz, 6H). hLPAi IC50 = 29 nM.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1250967-81-7, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; WANG, Ying; CHENG, Peter Tai Wah; LI, Jun; WALKER, Steven J.; (147 pag.)WO2019/126089; (2019); A1;,
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