Name: 1799610-97-1|5-Bromo-4-chloro-6-(5-fluorofuran-2-yl)thieno[2,3-d]pyrimidine|85%
Brand: Ambeed
SKU: A113221
Price: 59.0 USD
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Yield	Reaction Conditions	Operation in experiment
45%	With palladium diacetate; caesium carbonate; tert-butyl XPhos In tetrahydrofuran at 70℃; for 3h; Inert atmosphere; Darkness;
	With palladium diacetate; caesium carbonate; tert-butyl XPhos In tetrahydrofuran; water at 70℃; Inert atmosphere;	2b 5-Bromo-4-chloro-6-(5-fluoro-2-fnryl)thieno f 2,3-ti] pyrimidine 112.6 g (300 inmol) 5-bromo-4-chloro-6-iodo-thicno[2,3-d]pyrimidinc (Preparation la),254.4 g (1200 mmol) 2-(5-fluoro-2-furyl)-4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolane, 195.5 g(600 mmol) cesium carbonate, 3.36 g (15 mmol) Pd(OAc)2, 12.74 g (30 mmol) ‘BuX-Phoswere placed in a 2 L flask. 1000 mL THE and 400 mL water were added, and then stirredovernight at 70°C under argon atmosphere. THE was evaporated, and then the product was collected by filtration. Crude product was dissolved in THE, and then celite was added and the volatilcs were evaporated under reduced pressure. The solid residue was purified by flash chromatography on silica gel using hcptanc / EtOAc as clucnts. ‘H NMR (400 MHz, DMSO-d6): 8.95 (s, 1H), 7.55 (t, 111), 6.23 (dd, 11*1).
	With palladium diacetate; caesium carbonate; tert-butyl XPhos In tetrahydrofuran; water at 7℃; for 20h;	16.B B. Compound 44 (3.75 g, 10.0 mmol), reagent 45 (8.48 g, 40 mmol), CsCO3 (6.52 g, 20.0 mmol), Pd(OAc) 2 (112 mg, 0.5 mmol),tBuX-Phos (477 mg, 1 mmol) was added to THF (33 mL) and water(13mL). The reaction mixture was stirred at 70 ° C for 20 h. The THF was distilled off.The crude solid product was collected by filtration and purified by silica gel column chromatography(0-80% EtOAc/hexane)Purification afforded compound 46.

With palladium diacetate; caesium carbonate; tert-butyl XPhos In tetrahydrofuran; water at 70℃; for 20h;

16.B Compound 44 (3.75 g, 10.0 mmol), reagent 45 (8.48 g, 40 mmol), CsCO3 (6.52 g, 20.0 mmol), Pd(OAc)2 (112 mg, 0.5 mmol), tBuX-Phos (477 Mg, 1 mmol) was added to THF (33 mL) and distilled water (13 mL). The reaction mixture was stirred at 70° C. for 20 h. Then THF was evaporated, and the crude solid was collected by filtration. Finally, the residue was purified (0-80% EtOAc/hexane) by silica gel column chromatography to obtain Compound 46. ES/MS: m/z: 332 [M+H]+.

Reference： [1]Szlavik, Zoltan; Csekei, Marton; Paczal, Attila; Szabo, Zoltan B.; Sipos, Szabolcs; Radics, Gabor; Proszenyak, Agnes; Balint, Balazs; Murray, James; Davidson, James; Chen, Ijen; Dokurno, Pawel; Surgenor, Allan E; Daniels, Zoe Marie; Hubbard, Roderick E.; Le Toumelin-Braizat, Gaëtane; Claperon, Audrey; Lysiak-Auvity, Gaëlle; Girard, Anne-Marie; Bruno, Alain; Chanrion, Maia; Colland, Frédéric; Maragno, Ana-Leticia; Demarles, Didier; Geneste, Olivier; Kotschy, Andras [Journal of Medicinal Chemistry, 2020, vol. 63, # 22, p. 13762 - 13795]
[2]Current Patent Assignee: SERVIER MONDE; LIGAND PHARMACEUTICALS INC - WO2015/97123, 2015, A1 Location in patent: Page/Page column 38; 39
[3]Current Patent Assignee: HENAN MATTEL BIO PHARMACEUTICAL - CN108424417, 2018, A Location in patent: Paragraph 0099; 0100; 0102
[4]Current Patent Assignee: HENAN GENUINE BIOTECH - US2019/330230, 2019, A1 Location in patent: Paragraph 0069; 0071

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