Related Products of 941685-26-3 , The common heterocyclic compound, 941685-26-3, name is 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine, molecular formula is C12H18ClN3OSi, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Step 1: (3aS,7aS and 3aR,7aR) tert-butyl 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate To a stirred solution of Intermediate 2a (0.700 g, 2.47 mmol) and (3aS,7aS and 3aR,7aR) tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (HOAc salt; 0.918 g, 3.21 mmol; Intermediate 1a process, Step 4) in DMF (14 mL) was added TEA (1.03 mL, 7.40 mmol). The resulting reaction mixture was stirred at 90 C overnight. The reaction mixture was partitioned between EtOAc and 10% aqueous sodium chloride and the organic layer was washed with additional 10% aqueous sodium chloride. The first aqueous layer was extracted with additional EtOAc and the combined organic washings were dried over sodium sulfate and filtered. Silica gel was added to the filtrate and the mixture was concentrated in vacuo to a crude solid. The resulting solid was purified by column chromatography on silica gel, eluting with EtOAc/hexane (12-100%) to afford the desired product. LRMS calc’d for C24H40N5O3Si [M+H]+, 474; found 474. 1H NMR (500 MHz, DMSO-D6) delta 8.20 (s, 1H), 7.35 (d, 1H), 6.69 (d, 1H), 5.50 (s, 2H), 5.13 (br m, 1H), 4.59 (br d, 1H), 3.80-3.68 (br m, 1H), 3.47 (t, 2H), 3.41-3.32 (br m, 2H), 3.05 (br t, 1H), 2.09 (br m, 2H), 1.99 (br m, 1H), 1.75 (br m, 1H), 1.39 (overlapping s, m, 11H), 0.80 (t, 2H), -0.10 (s, 9H).
The synthetic route of 941685-26-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Merck Sharp & Dohme Corp.; GUERIN, David Joseph; BRUBAKER, Jason, D.; MARTINEZ, Michelle; JUNG, Joon, O.; ANTHONY, Neville, J.; SCOTT, Mark, E.; HOFFMAN, Dawn Marie Mampreian; WOO, Hyun Chong; DINSMORE, Christopher, J.; (75 pag.)EP2629777; (2018); B1;,
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