Diisobutylaluminumhydride → HCID 57419934, compound
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11](OC)=[O:12])[S:5][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:15]=[CH:16][N:17]=2)[S:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Charged a flask with methyl 2-(4-methylthiazol-2-ylamino)isonicotinate (0.5 g, 2.01 mmol) and added ether (10 mL). The reaction mixture was cooled to 0° C. and diisobutylaluminum hydride (8.01 mL, 8.01 mmol) was added. The reaction mixture was stirred at 0° C. for 8 hours and then stirred overnight at room temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated. The residue was purified using silica gel column chromatography with ethyl acetate as the eluent to afford (2-(4-methylthiazol-2-ylamino)pyridin-4-yl)methanol (0.347 g, 76.6% yield) as white solid. 1H NMR (CD3OD) δ 8.20 (d, 1H), 7.01 (m, 1H), 6.86 (m, 1H), 6.42 (m, 1H), 4.60 (s, 2H), 2.27 (d, 3H); Mass spectrum (apci) m/z=222 (55) (M+H).