Potassium Acetate → HCID 59514489, Verbindung

Reaktionsgleichung

Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[N:3]=1.C([O-])(=O)C.[K+]>CO.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:4]2[N:5]=[C:6]([N:13]([CH3:15])[CH3:14])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:2][N:3]=2)=[CH:22][CH:21]=1

Komponenten

Versuchsvorschrift

A suspension of methyl [4-chloro-6-(dimethylamino)-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (3.00 g, 8.22 mmol) and potassium acetate (2.42 g, 24.7 mmol) in methanol (30 mL) was treated with 10% Pd/C (1.00 g). The resulting black suspension was stirred under an atmosphere of hydrogen for 15 hours and then filtered over Celite. The residue was rinsed with methanol and the filtrate concentrated to dryness before partitioning between EtOAc and water. The separated organic layer was sequentially washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Chromatographic purification (silica gel, 1% MeOH in CHCl3) of the thus obtained crude product then yielded methyl [2-(4-aminobenzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (2.40 g, 97% yield) as a brown oil.