Sodium borohydride → HCID 25213707, compound
Reaction equation
[CH2:1]([N:3]1[C:8]([C:9]([C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH3:19])[CH:18]=2)[C:14]#[N:15])=[O:10])=[C:7]([CH:20]([CH3:22])[CH3:21])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([N:3]1[C:8]([CH:9]([OH:10])[C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH3:19])[CH:18]=2)[C:14]#[N:15])=[C:7]([CH:20]([CH3:21])[CH3:22])[C:6](=[O:23])[NH:5][C:4]1=[O:24])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (3) (0.700 g, 2.15 mmol) in ethanol (61 mL) at 0° C. was added sodium borohydride (0.081 g, 2.15 mmol) and the reaction mixture was stirred at 0° C. for 2 h, then at room temperature overnight. More sodium borohydride (0.081 g, 2.15 mmol). was then added, and the mixture was stirred for 24 h. More sodium borohydride (0.081 g, 2.15 mmol) was again added, and stirring was continued for 6 h. The reaction mixture was concentrated and quenched with saturated NH4Cl solution, acidified with 1N HCl and then extracted with ethyl acetate (2×). The combined organic layer dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 30 to 60% ethyl acetate/hexane) to give impure product. The impure product was purified again by flash column chromatography (silica gel, 0 to 5% methanol/dichloromethane), followed by purified by flash column chromatography (silica gel, 40 to 60% ethyl acetate/hexane) to give a white solid (0.31 g, 44%). 1H NMR (300 MHz, CD3OD): 7.55 (s, 1H), 7.47 (s, 1H), 7.43 (s, 1 H), 6.18 (s, 1H), 3.73 (q, J=6.9 Hz, 2H), 3.12-3.07 (m, 1H), 2.37 (s, 3H), 1.30 (d, J=7.2 Hz, 3H), 1.11 (d, J=6.6 Hz, 3H), 0.92-0.84 (m, 3H); Mass Spectrum: 328.1 (M+H).