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. 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, A new synthetic method of this compound is introduced below., Quality Control of 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
To a mixture of tert-butyl (S)-2-amino-4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino) butanoate (149 mg, 344 mumol) and 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (48 mg, 286.40 mumol) in t-AmOH (3 mL) was added 2.0M t-BuONa in THF (286 muL, 572 mumol) and tBuXPhos-Pd-G3 (23 mg, 29 mumol) and the resulting mixture was heated to 100 C. for 15 h. The reaction mixture was cooled to rt and then concentrated in vacuo to give a (S)-tert-butyl 4-(((R)-2-methoxypropyl) (4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl) butyl)amino)-2-((7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl) amino) butanoate intermediate, LCMS (ESI+): m/z=566.5 (M+H)+, which was used without further purification. Of the butanoate intermediate, 80 mg, 141 mumol, was taken up in DCM (1 mL) and TFA (400 muL) and the resulting mixture was stirred at rt for 6 h and then concentrated in vacuo. The crude residue was purified by chiral SFC to give a first fraction containing the title compound. LCMS (ESI+): m/z=510.3 (M+H)+. 1H NMR (400 MHz, Methanol-d4) delta ppm 8.18 (s, 1H) 7.19 (d, J=7.28 Hz, 1H) 7.08 (d, J=3.53 Hz, 1H) 6.59 (d, J=3.53 Hz, 1H) 6.40 (d, J=7.28 Hz, 1H) 4.61 (t, J=6.17 Hz, 1H) 3.76 (s, 4H) 3.34-3.40 (m, 3H) 3.33 (s, 3H) 3.22-3.29 (m, 1H) 2.99-3.19 (m, 4H) 2.69 (t, J=6.17 Hz, 2H) 2.58 (br s, 2H) 2.32-2.43 (m, 1H) 2.11-2.21 (m, 1H) 1.86 (dt, J=11.52, 6.04 Hz, 2H) 1.74 (br s, 4H) 1.16 (d, J=5.95 Hz, 3H).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; Pliant Therapeutics, Inc.; CHA, Jacob; DONG, Chengguo; HOM, Timothy; JIANG, Lan; LEFTHERIS, Katerina; LI, Hui; MORGANS, JR., David J.; MUNOZ, Manuel; REILLY, Maureen; ZHENG, Yajun; (232 pag.)US2019/276449; (2019); A1;,
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