Lithium borohydride → HCID 178418978, compound
Reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1)=O.[BH4-].[Li+]>C1COCC1>[OH:2][CH2:3][C:5]1[N:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:16][CH:17]=2)[N:8]=[C:7]([NH:23][C:24]2[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=2)[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of [6-methoxycarbonyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (2 g, 4.85 mmol) in THF (100 mL) is added lithium borohydride (0.32 g, 14.5 mmol). The reaction mixture is stirred at 50° C. for 1.5 hours. The reaction is then quenched with dilute HCl and extracted with ethyl acetate. The organic layer is successively washed with aqueous saturated NaHCO3 and brine, dried over MgSO4 and evaporated. The solid residue is triturated in ethyl acetate and the resulting white solid is collected by filtration to give the desired product [6-hydroxymethyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.