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. 1250967-81-7, name is 2-Chloro-4-isopropoxypyrimidine. A new synthetic method of this compound is introduced below., name: 2-Chloro-4-isopropoxypyrimidine
A mixture of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (5 mg, 8 pmol), 18F (15 mg, 0.04 mmol) ,2-chloro-4-isopropoxypyrimidine (8 mg, 0.05 mmol), BINAP (5 mg, 8 pmol), Pd2(dba)3 (2 mg, 4 pmol) and Cs2C03 (20 mg, 0.06 mmol) in toluene (1 mL) was heated in a sealed tube to 110 C overnight, then was cooled to RT and concentrated in vacuo. The residue was dissolved in THF (0.5 mL), MeOH (0.5 mL), and H20 (0.5 mL). LiOH.H20 (17 mg, 0.4 mmol) was added and the reaction was stirred at RT for 14 h, then was concentrated in vacuo. The residue was taken up in EtOAc (2 mL)/H20 (1 mL), and the solution was adjusted to pH ~ 5 with IN aq. HC1. The mixture was extracted with EtOAc (3 x 2 mL); the combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue was dissolved in DMF and purified via preparative LC/MS: Column: XBridge Cl 8, 200 mm x 19 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: a 0-min hold at 18% B, 18-58% B over 20 min, then a 4-min hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound (bis-TFA salt, 1 mg, 3% yield; 84% purity by LC-MS). LCMS, [M + H]+ = 468.4. NMR (500 MHz, DMSO-de) d 8.31 (s, 1H), 8.08 (d, J= 5.7 Hz, 1H), 7.92 (s, 1H), 6.18 (d, J= 5.7 Hz, 1H), 5.10 – 4.98 (m, 1H), 4.75 (s, 1H), 3.72 (s, 3H), 2.68 – 2.59 (m, 1H), 2.27 (s, 3H), 2.01 – 1.47 (m, 8H), 1.21 – 1.15 (m, 6H). hLPAi IC50 = 1014 nM.
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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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