With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.
Example 193 : (R)-N-( 1 -Methyl- 1 H-pyrazo 1-4-yl)- 1 -((6-((tetrahydrofuran-2- yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine(R)-(Tetrahydrofuran-2-yl)methanol (22mg, 0.214mmol) was added to a solution of NaH (lOmg, 0.246mmol) in dry DMF (ImL) in a 2-necked flask under Nitrogen. Another portion of NaH (lOmg, 0.246mmol) was added to a stirring solution of l-((6-fluoropyridin-2- yl)methyl)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 H-pyrazolo [3 ,4-d]pyrimidin-6-amine (Example 170) (50mg, 0.154mmol) in DMF (1ml). This solution was added to the 2-necked flask and stirred for 16h at rt. The reaction was quenched with NH4C1 (sat. solution, ImL) and diluted with Ethyl Acetate (20mL). The organics were separated and washed with NaHC03 (sat. solution, 20mL). The aqueous phase was re-extracted with Ethyl Acetate (2 x lOmL). The combined organics were dried over Na2S04, filtered and the solvent evaporated to give a crude product that was purified by prep HPLC. (R)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 -((6- ((tetrahydrofuran-2-yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine was obtained as a white solid (24mg, 38% yield). 1H NMR (d6-Acetone) delta 8.87 (s, 1H), 8.04 (s, 1H), 7.99 (s, 1H), 7.61 (s and t, 2H), 6.70 (d, 1H), 6.64 (d, 1H), 5.54 (s, 2H), 4.07 (m, 3H), 3.82 (s, 3H), 3.75 (m, 1H), 3.61 (m, 1H), 1.84 (m, 3H), 1.54 (m, 1H); LC-MS method B, (ES+) 407.1, RT = 7.65min., 97-99-4
The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); A1;,
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