Tetrahydrofuran → (6-Aminopyridin-3-yl)methanol
Reaction equation
P(C[C:6]1[N:11]2C=C(C(O)=O)[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)(O)(O)=O.[O:18]1CCC[CH2:19]1>>[NH2:14][C:10]1[N:11]=[CH:6][C:7]([CH2:19][OH:18])=[CH:8][CH:9]=1Participants
3
Procedure
A 250 mL 3-neck flask equipped with an addition funnel, an argon (Ar) inlet and a stopper was flame dried and cooled to room temperature. Dry tetrahydrofuran (THF, 30 mL) was added to the flask, followed by 1M. lithium aluminum hydride (LAH) in Et2O (16 mL). After cooling the solution to 0° C. with a wet ice/water bath, the product from Example 8 (0.92 g, 6 mmol) suspended in THF (100 mL) was added dropwise. The reaction was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with H2O, the salts filtered off and the filtrate stripped to give 0.591 g (99%) of title material.
Workup
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