HCID 59514516, compound → HCID 59514565, compound

HRID 2422158Notes

Reaction equation

HRID 2422158 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:6]([N:24]([CH3:26])[CH3:25])=[N:7][C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[N:9][C:10]=1[N:11]([CH3:13])[CH3:12].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[C:6]([N:24]([CH3:25])[CH3:26])=[N:7][C:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)=[N:9][C:10]=1[N:11]([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 59514516HCID 59514516, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59514565HCID 59514565, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3909dc2281184aeb9d1a4bf3b951b2f5
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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