HCID 59514516, compound → HCID 59514565, compound

Reaction equation

[CH3:1][N:2]([CH3:27])[C:3]1[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:7]([N:14]([CH3:16])[CH3:15])[N:6]=[C:5]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[N:4]=1.[H][H]>CO.[Pd]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:5]2[N:6]=[C:7]([N:14]([CH3:16])[CH3:15])[C:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:3]([N:2]([CH3:1])[CH3:27])[N:4]=2)=[CH:23][CH:22]=1

Participants

Procedure

A solution of methyl [4,6-bis(dimethylamino)-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (5.00 g, 13.39 mmol) in methanol (150 mL) was treated with palladium on charcoal (10% Pd, 0.50 g) and the resulting black suspension was stirred under a blanket of hydrogen gas at room temperature for 10 hours. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to give methyl [2-(4-aminobenzyl)-4,6-bis(dimethylamino)pyrimidin-5-yl]acetate (4.53 g, 98%).