Aluminium lithium hydride → HCID 86629465, compound
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([NH:10][C:11]1[C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=[C:13]([N:22]([O:24][CH3:25])[CH3:23])[CH:12]=1)([CH3:9])[CH3:8]>C1COCC1>[CH:7]([NH:10][C:11]1[CH:12]=[C:13]([N:22]([O:24][CH3:25])[CH3:23])[N:14]=[CH:15][C:16]=1[CH2:17][OH:18])([CH3:9])[CH3:8]Participants
4
Procedure
LiAlH4 (0.9 g, 24.0 mmol) was added in portions to a solution of ethyl 4-(isopropylamino)-6-(methoxy(methyl)amino)nicotinate (3.2 g, 12.0 mmol) in THF (60 mL) at 0° C. and the resultant reaction mixture was stirred at RT for 30 min. The reaction was quenched by the addition of water (1 mL) and aqueous 2N NaOH (1 mL). The resulting precipitates were removed by filtration and the filtrate was concentrated to afford (4-(isopropylamino)-6-(methoxy(methyl)amino)pyridine-3-yl)methanol (2.9 g, >100% yield), which was used without further purification. 1HNMR (400 MHz, DMSO-d6): δ 7.62 (s, 1 H), 6.16 (s, 1 H), 5.44 (d, J=7.2 Hz, 1 H), 5.02 (bs, 1 H), 4.33 (s, 2 H), 3.69-3.61 (m, 4 H), 3.06 (s, 3 H), 1.18 (d, J=6.4 Hz, 6 H).