97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,97-99-4
To a solution of (2R)-tetrahydrofuran-2-ylmethanol (58 mg, 0.57 mmol) in dry DMF (5 mL) was added NaH (23 mg, 60% in mineral oil, 0.57 mmol) under a N2 atmosphere. After the addition, the reaction mixture was stirred at room temperature for 1 hr. Then, to the mixture was added (2R)-2-[({2-chloro-6-[4-(1 /-/-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]pyrimidin-4- yl}carbonyl)amino]propyl benzoate (1-183) (100 mg, 0.19 mmol). After the addition, the resulting mixture was heated at 50 C for 4 hr. LCMS showed the reaction was completed. The mixture was cooled to room temperature and quenched with H20 (20 mL). The mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (4 x 50 mL), dried over Na2S04 and concentrated to give the residue, which was purified by silica gel chromatography (CH2CI2/MeOH = 10/1 , Rf ~ 0.6) to give the crude product, which was further purified with preparative HPLC(Column: Phenomenex Gemini C18 250 x 21 .2 mm, deltamuetaiota. Mobile phase: from 20% MeCN (0.225% HCOOH) in water to 40% MeCN (0.225% HCOOH) in water. Wavelength: 220 nm) Lyophilization afforded N-[(2f?)-1 -hydroxypropan-2-yl]-6-[4-(1 H- pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]-2-[(2R)-tetrahydrofuran-2-ylmethoxy]pyrimidine-4- carboxamide (Example 80) (20.1 mg, 22%) as a white solid. LCMS (APCI), m/z 482.2 [M + H]+; (400 MHz, DMSO-c/s) 8 ppm 13.29 (br. s., 1 H), 8.48 – 8.49 (m, 1 H), 8.31 (d, J = 8.0 Hz, 1 H), 8.18 (d, J = 8.8 Hz, 1 H), 7.13 -7.16 (m, 1 H), 7.04 (s, 1 H), 4.89 (t, J = 5.5 Hz, 1 H), 4.50 (br. s., 1 H), 4.26 (d, J = 5.5 Hz, 2 H), 4.12 – 4.18 (m, 1 H), 4.03 – 4.04 (m, 1 H), 3.77 – 3.82 (m, 1 H), 3.65 -3.70 (m, 1 H), 3.42 – 3.47 (m, 3 H), 3.16 – 3.23 (m, 2 H), 3.00 (br. s., 1 H), 2.12 (d, J = 1 1 Hz, 2 H), 1.96 – 2.04 (m, 1 H), 1 .81 -1 .88 (m, 4 H), 1 .62 – 1 .71 (m, 1 H), 1 .15 (d, J = 6.5 Hz, 3 H).
The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
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