Aluminium lithium hydride → tert-Butyl 5-(2-(1-amino-2-methylpropan-2-yl)-pyridin-4-yl)-4-methylthiazol-2-ylcarbamate
반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:31])[NH:13][C:14]1[S:15][C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:28])[CH3:27])[CH:21]=2)=[C:17]([CH3:19])[N:18]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12](=[O:31])[NH:13][C:14]1[S:15][C:16]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([C:26]([CH3:28])([CH3:27])[CH2:29][NH2:30])[CH:21]=2)=[C:17]([CH3:19])[N:18]=1)([CH3:8])([CH3:10])[CH3:9]참가 물질
4
실험 절차
LiAlH4 (1M in THF, 3.06 mL, 3.06 mmol, 1.5 eq) is added to a solution of {5-[2-(cyano-dimethyl-methyl)-pyridin-4-yl]-4-methyl-thiazol-2-yl}-carbamic acid tert-butyl ester (Step 21.4) (0.73 g, 2.04 mmol) in THF (10 mL), under an argon atmosphere. The reaction mixture is stirred for 2 h at rt, quenched by addition of H2O (20 mL) and extracted with EtOAc (2×75 mL). The organic phase is washed with a saturated solution of NaHCO3 (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH/NH3aq, 99:0:1→94:5:1) to afford 318 mg of the title compound as a brown solid: ESI-MS: 363.1 [M+H]+; TLC: Rf=0.11 (DCM/MeOH, 9:1).